Air oxidation method employed for the disulfide bond formation of natural and synthetic peptides (604 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2015; 47(8): 1507-1515.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 3.196, 5-year impact factor: 3.064
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84928142537&partnerID=40&md5=2511ec3a03f0e922a371aa1b97a1a3ee
Keywords: Disulfide Bridges, Native-Like Oxidation Conditions, Oxidation Methods, Peptide Folding, Arginylalanylcystylarginylhistidyltryptophylcysteine, Arginylalanylcystylarginylphenylalanylphenylalanylcysteine, Arginylalanylcystylarginyltyrosyltryptophylcysteine, Chemokine Receptor Cxcr4 Antagonist, Cystyltryptophylhistidylarginylcysteine, Distinctin, Homodimer, Unclassified Drug, Air Oxidation, Article, Chemical Modification, Chemical Phenomena, Concentration (parameters), Cyclization Reaction, Disulfide Bond, Molecular Dynamics, Peptide Synthesis, Priority Journal, Protein Conformation, Protein Folding,
Affiliations:
*** IBB - CNR ***
Institute of Biostructures and Bioimaging, National Research Council, Naples, Italy
Institute of Biomolecular Chemistry, National Research Council, Pozzuoli, Naples, Italy
Proteomics and Mass Spectrometry Laboratory, National Research Council, Naples, Italy
References:
Akaji, K., Kiso, Y., Synthesis of cystine peptides (2002) Houben-Weyl: Methods of Organic Chemistry, pp. 101-141. , M. Goodman A. Felix L. Moroder C. Toniolo (eds) Synthesis of peptides and peptidominetics, Thieme E22b Stuttgart Germany, New Yor
Andreu, D., Albericio, F., Sole, N.A., Munson, M.C., Ferrer, M., Barany, G., (1994) Peptide Synthesis Protocols, pp. 91-169. , 35 Humana Press Totowa
Annis, I., Hargittai, B., Barany, G., Disulfide bond formation in peptides (1997) Methods Enzymol, 289, pp. 198-221. , 1:CAS:528:DyaK2sXotVyksr8%3D 9353723
Becucci, L., Papini, M., Mullen, D., Scaloni, A., Veglia, G., Guidelli, R., Probing membrane permeabilization by the antimicrobial peptide distinctin in mercury-supported biomimetic membranes (2011) Biochim Biophys Acta, 1808, pp. 2745-2752. , 1:CAS:528:DC%2BC3MXhtFSjs7rK 21824466
Berendsen, H.J.C., Postma, J.P.M., Van Gunsteren, W.F., Dinola, A., Haak, J.R., Molecular dynamics with coupling to an external bath (1984) J Chem Phys, 81, pp. 3684-3690. , 1:CAS:528:DyaL2cXmtlGksbY%3D
Buchner, J., Moroder, L., (2009) Oxidative Folding of Peptides and Proteins, pp. 274-380. , RSC Biomolecular Sciences Cambridge
Calce, E., Sandomenico, A., Saviano, M., Ruvo, M., De Luca, S., Cysteine co-oxidation process driven by native peptide folding: An example on HER2 receptor model system (2014) Amino Acids, 46, pp. 1197-1206. , 1:CAS:528:DC%2BC2cXhs1Kjsrg%3D 24493095
Case, D.A., Darden, T.A., Cheatham, T.E., III, Simmerling, C.L., Wang, J., Duke, R.E., Luo, R., Kollman, P.A., (2012) AMBER 12, , University of California San Francisco
Chan, W.C., White, P.D., (2000) Fmoc Solid Phase Peptide Synthesis, A Practical Approach, , Oxford University Press Cary
Cirioni, O., Ghiselli, R., Orlando, F., Silvestri, C., De Luca, S., Salzano, A.M., Mocchegiani, F., Giacometti, A., Efficacy of the amphibian peptide distinctin in a neutropenic mouse model of staphylococcal sepsis (2008) Crit Care Med, 36, pp. 2629-2633. , 1:CAS:528:DC%2BD1cXhtVejs7fI 18679116
Creighton, T.E., Disulphide bonds and protein stability (1988) BioEssays, 8, pp. 57-63. , 1:CAS:528:DyaL1cXhsVGmsL4%3D 3282505
Dalla Serra, M., Cirioni, O., Vitale, R.M., Renzone, G., Coraiola, M., Giacometti, A., Potrich, C., Scaloni, A., Structural features of distinctin affecting peptide biological and biochemical properties (2008) Biochemistry, 47, pp. 7888-7899. , 1:CAS:528:DC%2BD1cXnvF2gtbo%3D 18597491
Ellman, G.L., Tissue sulfhydryl groups (1959) Arch Biochem Biophys, 82, pp. 70-77. , 1:CAS:528:DyaG1MXotl2ksA%3D%3D 13650640
Engebretsen, M., Agner, E., Sandosham, J., Fischer, P.M., Unexpected lability of cysteine acetamidomethyl thiol protecting group. Tyrosine ring alkylation and disulfide bond formation upon acidolysis (1997) J Pept Res, 49, pp. 341-346. , 1:CAS:528:DyaK2sXjsVGksL4%3D 9176818
Eritja, R., Ziehler-Martin, J.P., Walker, P.A., Lee, T.D., Legesse, K., Albericio, F., Kaplan, B.E., On the use of S-t-butylsulphenyl group for protection of cysteine in solid-phase peptide synthesis using Fmoc-amino acids (1987) Tetrahedron, 43, pp. 2675-2680. , 1:CAS:528:DyaL1cXhtFaqtr4%3D
Essmann, U., Perera, L., Berkowitz, M.L., Darden, T., Lee, H., Pedersen, L.G., A smooth particle mesh Ewald method (1995) J Chem Phys, 103, pp. 8577-8593. , 1:CAS:528:DyaK2MXptlehtrw%3D
Evaristo, G., Pinkse, M., Wang, L., Zhou, M., Wu, Y., Wang, H., Chen, T., Verhaert, P., The chains of the heterodimeric amphibian skin antimicrobial peptide, distinctin, are encoded by separate messenger RNAs (2013) J Proteomics, 78, pp. 245-253. , 1:CAS:528:DC%2BC38XhvVOjs7zK 23017495
Giacometti, A., Cirioni, O., Ghiselli, R., Orlando, F., Silvestri, C., Renzone, G., Testa, I., Scalise, G., Distinctin improves the efficacies of glycopeptides and betalactams against staphylococcal biofilm in an experimental model of central venous catheter infection (2007) J Biomed Mater Res A, 81, pp. 233-239. , 17120214
Jorgensen, W.L., Chandrasekhar, J., Madura, J.D., Impey, R.W., Klein, M.L., Comparison of simple potential functions for simulating liquid water (1983) J Chem Phys, 79, pp. 926-935. , 1:CAS:528:DyaL3sXksF2htL4%3D
Kamber, B., Hartmann, A., Eisler, K., Riniker, B., Rink, H., Sieber, P., Rittel, W., The synthesis of cystine peptides by iodine oxidation of s-trityl-cysteine and s-acetamidomethyl-cysteine peptides (1980) Helv Chim Acta, 63, pp. 899-915. , 1:CAS:528:DyaL3MXms1ShsA%3D%3D
Kimura, T., Synthesis of cystine peptides (2002) Houben-Weyl Methods of Organic Chemistry, pp. 142-161. , M. Goodman A. Felix L. Moroder C. Toniolo (eds) Synthesis of Peptides and Peptidominetics Thieme E22b Stuttgart, Germany New York
Kudryavtseva, E.V., Sidorova, M.V., Evstigneeva, R.P., Some peculiarities of synthesis of cysteine-containing peptides (1998) Russ Chem Rev, 67, pp. 545-562
Liu, F., Liu, Q., Mezo, A.R., An iodine-free and directed-disulfide-bond-forming route to insulin analogues (2014) Org Lett, 16, pp. 3126-3129. , 1:CAS:528:DC%2BC2cXos1Wlurk%3D 24856301
Matsumura, M., Signor, G., Matthews, B.W., Substantial increase of protein stability by multiple disulphide bonds (1989) Nature, 342, pp. 291-293. , 1:CAS:528:DyaK3cXjt1entg%3D%3D 2812028
Mullen, D.G., Verardi, R., Porcelli, F., Scaloni, A., Barany, G., Veglia, G., Synthesis and characterization of the 47-residue heterodimeric antimicrobial peptide distinctin, featuring directed disulfide bridge formation (2012) Biopolymers, 98, pp. 479-484. , 1:CAS:528:DC%2BC38XhsFGmu7zI 3551542 23203692
Pace, C.N., Grimsley, G.R., Thomson, J.A., Barnett, B.J., Conformational stability and activity of ribonuclease T1 with zero, one, and two intact disulfide bonds (1988) J Biol Chem, 263, pp. 11820-11825. , 1:CAS:528:DyaL1cXls1Kgt74%3D 2457027
Pettersen, E.F., Goddard, T.D., Huang, C.C., Couch, G.S., Greenblatt, D.M., Meng, E.C., Ferrin, T.E., UCSF Chimera - A visualization system for exploratory research and analysis (2004) J Comput Chem, 25, pp. 1605-1612. , 1:CAS:528:DC%2BD2cXmvVOhsbs%3D 15264254
Portella, L., Vitale, R., De Luca, S., D'Alterio, C., Ieranò, C., Napolitano, M., Riccio, A., Scala, S., Preclinical development of a novel class of CXCR4 antagonist impairing solid tumors growth and metastases (2013) PLoS One, 8 (9), p. e74548
Postma, T.M., Albericio, F., Disulfide Formation Strategies in Peptide Synthesis (2014) Eur J Org Chem, 17, pp. 3519-3530
Ragone, R., De, L.S., Tesauro, D., Pedone, C., Morelli, G., -2001) Fluorescence studies on the binding between 1-47 fragment of cholecystokinin receptor CCK (A)-R (1-47) and nonsulfated cholecystokinin octapeptide CCK8 (2000) Biopolymers, 56, pp. 47-53. , 1:CAS:528:DC%2BD3MXotFKjs7s%3D 11582577
Raimondo, D., Andreotti, G., Saint, N., Amodeo, P., Renzone, G., Sanseverino, M., Zocchi, I., Scaloni, A., A folding-dependent mechanism of antimicrobial peptide resistance to degradation unveiled by solution structure of distinctin (2005) Proc Natl Acad Sci USA, 102, pp. 6309-6314. , 1:CAS:528:DC%2BD2MXktlygsbg%3D 1088359 15840728
Reinwarth, M., Glotzbach, B., Tomaszowski, M., Fabritz, S., Avrutina, O., Kolmar, H., Oxidative folding of peptides with cystine-knot architectures: Kinetic studies and optimization of folding conditions (2013) ChemBioChem, 14, pp. 137-146. , 1:CAS:528:DC%2BC38XhvVWjur3I 23229141
Ryckaert, J.-P., Ciccotti, G., Berendsen, H.J., Numerical integration of the cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes (1977) J Comput Phys, 23, pp. 327-341. , 1:CAS:528:DyaE2sXktVGhsL4%3D
Sheppard, R.C., Williams, B.J., Acid-labile resin linkage agents for use in solid phase peptide synthesis (1982) Int J Pept Protein Res, 20, pp. 451-454. , 1:CAS:528:DyaL3sXht1Klsrw%3D 7174209
Simonetti, O., Cirioni, O., Ghiselli, R., Goteri, G., Orlando, F., Monfregola, L., De Luca, S., Scaloni, A., Antimicrobial properties of distinctin in an experimental model of MRSA-infected wounds (2012) Eur J Clin Microbiol Infect Dis, 31, pp. 3047-3055. , 1:CAS:528:DC%2BC38XhsFKlu7%2FM 22729599
Steiner, A.M., Bulaj, G., Optimization of oxidative folding methods for cysteine-rich peptides: A study of conotoxins containing three disulfide bridges (2011) J Pept Sci, 17, pp. 1-7. , 1:CAS:528:DC%2BC3cXhsFyjtbzI 20814907
Tam, J.P., Wu, C.R., Liu, W., Zhang, J.W., Disulfide bond formation in peptides by dimethyl sulfoxide. Scope and applications (1991) J Am Chem Soc, 113, pp. 6657-6662. , 1:CAS:528:DyaK3MXkvFaqs7s%3D
Thornton, J.M., Disulphide bridges in globular proteins (1981) J Mol Biol, 151, pp. 261-287. , 1:CAS:528:DyaL38XkslyisQ%3D%3D 7338898
Verardi, R., Traaseth, N.J., Shi, L., Porcelli, F., Monfregola, L., De Luca, S., Amodeo, P., Scaloni, A., Probing membrane topology of the antimicrobial peptide distinctin by solid-state NMR spectroscopy in zwitterionic and charged lipid bilayers (2011) Biochim Biophys Acta, 1808, pp. 34-40. , 1:CAS:528:DC%2BC3cXhsFart7fM 2997851 20719234
Wedemeyer, W.J., Welker, E., Narayan, M., Scheraga, H.A., Disulfide bonds and protein folding (2000) Biochemistry, 39, pp. 4207-4216. , 1:CAS:528:DC%2BD3cXhsl2hu7Y%3D 10757967
Zhang, S., Lin, F., Hossain, M.A., Shabanpoor, F., Tregear, G.W., Wade, J.D., Simultaneous post-cysteine(S-Acm) group removal quenching of iodine and isolation of peptide by one step ether precipitation (2008) Int J Pept Res Ther, 14, pp. 301-305. , 1:CAS:528:DC%2BD1cXhsVKjt7%2FI
Zwanzig, R., Nonlinear generalized Langevin equations (1973) J Stat Phys, 9, pp. 215-220
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2015; 47(8): 1507-1515.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 3.196, 5-year impact factor: 3.064
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84928142537&partnerID=40&md5=2511ec3a03f0e922a371aa1b97a1a3ee
Keywords: Disulfide Bridges, Native-Like Oxidation Conditions, Oxidation Methods, Peptide Folding, Arginylalanylcystylarginylhistidyltryptophylcysteine, Arginylalanylcystylarginylphenylalanylphenylalanylcysteine, Arginylalanylcystylarginyltyrosyltryptophylcysteine, Chemokine Receptor Cxcr4 Antagonist, Cystyltryptophylhistidylarginylcysteine, Distinctin, Homodimer, Unclassified Drug, Air Oxidation, Article, Chemical Modification, Chemical Phenomena, Concentration (parameters), Cyclization Reaction, Disulfide Bond, Molecular Dynamics, Peptide Synthesis, Priority Journal, Protein Conformation, Protein Folding,
Affiliations:
*** IBB - CNR ***
Institute of Biostructures and Bioimaging, National Research Council, Naples, Italy
Institute of Biomolecular Chemistry, National Research Council, Pozzuoli, Naples, Italy
Proteomics and Mass Spectrometry Laboratory, National Research Council, Naples, Italy
References:
Akaji, K., Kiso, Y., Synthesis of cystine peptides (2002) Houben-Weyl: Methods of Organic Chemistry, pp. 101-141. , M. Goodman A. Felix L. Moroder C. Toniolo (eds) Synthesis of peptides and peptidominetics, Thieme E22b Stuttgart Germany, New Yor
Andreu, D., Albericio, F., Sole, N.A., Munson, M.C., Ferrer, M., Barany, G., (1994) Peptide Synthesis Protocols, pp. 91-169. , 35 Humana Press Totowa
Annis, I., Hargittai, B., Barany, G., Disulfide bond formation in peptides (1997) Methods Enzymol, 289, pp. 198-221. , 1:CAS:528:DyaK2sXotVyksr8%3D 9353723
Becucci, L., Papini, M., Mullen, D., Scaloni, A., Veglia, G., Guidelli, R., Probing membrane permeabilization by the antimicrobial peptide distinctin in mercury-supported biomimetic membranes (2011) Biochim Biophys Acta, 1808, pp. 2745-2752. , 1:CAS:528:DC%2BC3MXhtFSjs7rK 21824466
Berendsen, H.J.C., Postma, J.P.M., Van Gunsteren, W.F., Dinola, A., Haak, J.R., Molecular dynamics with coupling to an external bath (1984) J Chem Phys, 81, pp. 3684-3690. , 1:CAS:528:DyaL2cXmtlGksbY%3D
Buchner, J., Moroder, L., (2009) Oxidative Folding of Peptides and Proteins, pp. 274-380. , RSC Biomolecular Sciences Cambridge
Calce, E., Sandomenico, A., Saviano, M., Ruvo, M., De Luca, S., Cysteine co-oxidation process driven by native peptide folding: An example on HER2 receptor model system (2014) Amino Acids, 46, pp. 1197-1206. , 1:CAS:528:DC%2BC2cXhs1Kjsrg%3D 24493095
Case, D.A., Darden, T.A., Cheatham, T.E., III, Simmerling, C.L., Wang, J., Duke, R.E., Luo, R., Kollman, P.A., (2012) AMBER 12, , University of California San Francisco
Chan, W.C., White, P.D., (2000) Fmoc Solid Phase Peptide Synthesis, A Practical Approach, , Oxford University Press Cary
Cirioni, O., Ghiselli, R., Orlando, F., Silvestri, C., De Luca, S., Salzano, A.M., Mocchegiani, F., Giacometti, A., Efficacy of the amphibian peptide distinctin in a neutropenic mouse model of staphylococcal sepsis (2008) Crit Care Med, 36, pp. 2629-2633. , 1:CAS:528:DC%2BD1cXhtVejs7fI 18679116
Creighton, T.E., Disulphide bonds and protein stability (1988) BioEssays, 8, pp. 57-63. , 1:CAS:528:DyaL1cXhsVGmsL4%3D 3282505
Dalla Serra, M., Cirioni, O., Vitale, R.M., Renzone, G., Coraiola, M., Giacometti, A., Potrich, C., Scaloni, A., Structural features of distinctin affecting peptide biological and biochemical properties (2008) Biochemistry, 47, pp. 7888-7899. , 1:CAS:528:DC%2BD1cXnvF2gtbo%3D 18597491
Ellman, G.L., Tissue sulfhydryl groups (1959) Arch Biochem Biophys, 82, pp. 70-77. , 1:CAS:528:DyaG1MXotl2ksA%3D%3D 13650640
Engebretsen, M., Agner, E., Sandosham, J., Fischer, P.M., Unexpected lability of cysteine acetamidomethyl thiol protecting group. Tyrosine ring alkylation and disulfide bond formation upon acidolysis (1997) J Pept Res, 49, pp. 341-346. , 1:CAS:528:DyaK2sXjsVGksL4%3D 9176818
Eritja, R., Ziehler-Martin, J.P., Walker, P.A., Lee, T.D., Legesse, K., Albericio, F., Kaplan, B.E., On the use of S-t-butylsulphenyl group for protection of cysteine in solid-phase peptide synthesis using Fmoc-amino acids (1987) Tetrahedron, 43, pp. 2675-2680. , 1:CAS:528:DyaL1cXhtFaqtr4%3D
Essmann, U., Perera, L., Berkowitz, M.L., Darden, T., Lee, H., Pedersen, L.G., A smooth particle mesh Ewald method (1995) J Chem Phys, 103, pp. 8577-8593. , 1:CAS:528:DyaK2MXptlehtrw%3D
Evaristo, G., Pinkse, M., Wang, L., Zhou, M., Wu, Y., Wang, H., Chen, T., Verhaert, P., The chains of the heterodimeric amphibian skin antimicrobial peptide, distinctin, are encoded by separate messenger RNAs (2013) J Proteomics, 78, pp. 245-253. , 1:CAS:528:DC%2BC38XhvVOjs7zK 23017495
Giacometti, A., Cirioni, O., Ghiselli, R., Orlando, F., Silvestri, C., Renzone, G., Testa, I., Scalise, G., Distinctin improves the efficacies of glycopeptides and betalactams against staphylococcal biofilm in an experimental model of central venous catheter infection (2007) J Biomed Mater Res A, 81, pp. 233-239. , 17120214
Jorgensen, W.L., Chandrasekhar, J., Madura, J.D., Impey, R.W., Klein, M.L., Comparison of simple potential functions for simulating liquid water (1983) J Chem Phys, 79, pp. 926-935. , 1:CAS:528:DyaL3sXksF2htL4%3D
Kamber, B., Hartmann, A., Eisler, K., Riniker, B., Rink, H., Sieber, P., Rittel, W., The synthesis of cystine peptides by iodine oxidation of s-trityl-cysteine and s-acetamidomethyl-cysteine peptides (1980) Helv Chim Acta, 63, pp. 899-915. , 1:CAS:528:DyaL3MXms1ShsA%3D%3D
Kimura, T., Synthesis of cystine peptides (2002) Houben-Weyl Methods of Organic Chemistry, pp. 142-161. , M. Goodman A. Felix L. Moroder C. Toniolo (eds) Synthesis of Peptides and Peptidominetics Thieme E22b Stuttgart, Germany New York
Kudryavtseva, E.V., Sidorova, M.V., Evstigneeva, R.P., Some peculiarities of synthesis of cysteine-containing peptides (1998) Russ Chem Rev, 67, pp. 545-562
Liu, F., Liu, Q., Mezo, A.R., An iodine-free and directed-disulfide-bond-forming route to insulin analogues (2014) Org Lett, 16, pp. 3126-3129. , 1:CAS:528:DC%2BC2cXos1Wlurk%3D 24856301
Matsumura, M., Signor, G., Matthews, B.W., Substantial increase of protein stability by multiple disulphide bonds (1989) Nature, 342, pp. 291-293. , 1:CAS:528:DyaK3cXjt1entg%3D%3D 2812028
Mullen, D.G., Verardi, R., Porcelli, F., Scaloni, A., Barany, G., Veglia, G., Synthesis and characterization of the 47-residue heterodimeric antimicrobial peptide distinctin, featuring directed disulfide bridge formation (2012) Biopolymers, 98, pp. 479-484. , 1:CAS:528:DC%2BC38XhsFGmu7zI 3551542 23203692
Pace, C.N., Grimsley, G.R., Thomson, J.A., Barnett, B.J., Conformational stability and activity of ribonuclease T1 with zero, one, and two intact disulfide bonds (1988) J Biol Chem, 263, pp. 11820-11825. , 1:CAS:528:DyaL1cXls1Kgt74%3D 2457027
Pettersen, E.F., Goddard, T.D., Huang, C.C., Couch, G.S., Greenblatt, D.M., Meng, E.C., Ferrin, T.E., UCSF Chimera - A visualization system for exploratory research and analysis (2004) J Comput Chem, 25, pp. 1605-1612. , 1:CAS:528:DC%2BD2cXmvVOhsbs%3D 15264254
Portella, L., Vitale, R., De Luca, S., D'Alterio, C., Ieranò, C., Napolitano, M., Riccio, A., Scala, S., Preclinical development of a novel class of CXCR4 antagonist impairing solid tumors growth and metastases (2013) PLoS One, 8 (9), p. e74548
Postma, T.M., Albericio, F., Disulfide Formation Strategies in Peptide Synthesis (2014) Eur J Org Chem, 17, pp. 3519-3530
Ragone, R., De, L.S., Tesauro, D., Pedone, C., Morelli, G., -2001) Fluorescence studies on the binding between 1-47 fragment of cholecystokinin receptor CCK (A)-R (1-47) and nonsulfated cholecystokinin octapeptide CCK8 (2000) Biopolymers, 56, pp. 47-53. , 1:CAS:528:DC%2BD3MXotFKjs7s%3D 11582577
Raimondo, D., Andreotti, G., Saint, N., Amodeo, P., Renzone, G., Sanseverino, M., Zocchi, I., Scaloni, A., A folding-dependent mechanism of antimicrobial peptide resistance to degradation unveiled by solution structure of distinctin (2005) Proc Natl Acad Sci USA, 102, pp. 6309-6314. , 1:CAS:528:DC%2BD2MXktlygsbg%3D 1088359 15840728
Reinwarth, M., Glotzbach, B., Tomaszowski, M., Fabritz, S., Avrutina, O., Kolmar, H., Oxidative folding of peptides with cystine-knot architectures: Kinetic studies and optimization of folding conditions (2013) ChemBioChem, 14, pp. 137-146. , 1:CAS:528:DC%2BC38XhvVWjur3I 23229141
Ryckaert, J.-P., Ciccotti, G., Berendsen, H.J., Numerical integration of the cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes (1977) J Comput Phys, 23, pp. 327-341. , 1:CAS:528:DyaE2sXktVGhsL4%3D
Sheppard, R.C., Williams, B.J., Acid-labile resin linkage agents for use in solid phase peptide synthesis (1982) Int J Pept Protein Res, 20, pp. 451-454. , 1:CAS:528:DyaL3sXht1Klsrw%3D 7174209
Simonetti, O., Cirioni, O., Ghiselli, R., Goteri, G., Orlando, F., Monfregola, L., De Luca, S., Scaloni, A., Antimicrobial properties of distinctin in an experimental model of MRSA-infected wounds (2012) Eur J Clin Microbiol Infect Dis, 31, pp. 3047-3055. , 1:CAS:528:DC%2BC38XhsFKlu7%2FM 22729599
Steiner, A.M., Bulaj, G., Optimization of oxidative folding methods for cysteine-rich peptides: A study of conotoxins containing three disulfide bridges (2011) J Pept Sci, 17, pp. 1-7. , 1:CAS:528:DC%2BC3cXhsFyjtbzI 20814907
Tam, J.P., Wu, C.R., Liu, W., Zhang, J.W., Disulfide bond formation in peptides by dimethyl sulfoxide. Scope and applications (1991) J Am Chem Soc, 113, pp. 6657-6662. , 1:CAS:528:DyaK3MXkvFaqs7s%3D
Thornton, J.M., Disulphide bridges in globular proteins (1981) J Mol Biol, 151, pp. 261-287. , 1:CAS:528:DyaL38XkslyisQ%3D%3D 7338898
Verardi, R., Traaseth, N.J., Shi, L., Porcelli, F., Monfregola, L., De Luca, S., Amodeo, P., Scaloni, A., Probing membrane topology of the antimicrobial peptide distinctin by solid-state NMR spectroscopy in zwitterionic and charged lipid bilayers (2011) Biochim Biophys Acta, 1808, pp. 34-40. , 1:CAS:528:DC%2BC3cXhsFart7fM 2997851 20719234
Wedemeyer, W.J., Welker, E., Narayan, M., Scheraga, H.A., Disulfide bonds and protein folding (2000) Biochemistry, 39, pp. 4207-4216. , 1:CAS:528:DC%2BD3cXhsl2hu7Y%3D 10757967
Zhang, S., Lin, F., Hossain, M.A., Shabanpoor, F., Tregear, G.W., Wade, J.D., Simultaneous post-cysteine(S-Acm) group removal quenching of iodine and isolation of peptide by one step ether precipitation (2008) Int J Pept Res Ther, 14, pp. 301-305. , 1:CAS:528:DC%2BD1cXhsVKjt7%2FI
Zwanzig, R., Nonlinear generalized Langevin equations (1973) J Stat Phys, 9, pp. 215-220
Air oxidation method employed for the disulfide bond formation of natural and synthetic peptides
Among the available protocols, chemically driven approaches to oxidize cysteine may not be required for molecules that, under the native-like conditions, naturally fold in conformations ensuring an effective pairing of the right disulfide bridge pattern. In this contest, we successfully prepared the distinctin, a natural heterodimeric peptide, and some synthetic cyclic peptides that are inhibitors of the CXCR4 receptor. In the first case, the air oxidation reaction allowed to connect two peptide chains via disulfide bridge, while in the second case allowed the cyclization of rationally designed peptides by an intramolecular disulfide bridge. Computational approaches helped to either drive de-novo design or suggest structural modifications and optimal oxidization protocols for disulfide-containing molecules. They are able to both predict and to rationalize the propensity of molecules to spontaneously fold in suitable conformations to achieve the right disulfide bridges. © 2015 Springer-Verlag Wien.
Among the available protocols, chemically driven approaches to oxidize cysteine may not be required for molecules that, under the native-like conditions, naturally fold in conformations ensuring an effective pairing of the right disulfide bridge pattern. In this contest, we successfully prepared the distinctin, a natural heterodimeric peptide, and some synthetic cyclic peptides that are inhibitors of the CXCR4 receptor. In the first case, the air oxidation reaction allowed to connect two peptide chains via disulfide bridge, while in the second case allowed the cyclization of rationally designed peptides by an intramolecular disulfide bridge. Computational approaches helped to either drive de-novo design or suggest structural modifications and optimal oxidization protocols for disulfide-containing molecules. They are able to both predict and to rationalize the propensity of molecules to spontaneously fold in suitable conformations to achieve the right disulfide bridges. © 2015 Springer-Verlag Wien.
Air oxidation method employed for the disulfide bond formation of natural and synthetic peptides
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Air oxidation method employed for the disulfide bond formation of natural and synthetic peptides
Other filter: ([btitle,keywords] "Disulfide Bridges" O ...
Iaccarino E, Sandomenico A, Corvino G, Foca G, Severino V, Russo R, Caporale A, Raimondo D, D'Abramo M, Alba J, Chambery A, Ruvo M
* Investigating the oxidative refolding mechanism of Cripto-1 CFC domain (321 views)
Int J Biol Macromol (ISSN: 0141-8130linking, 1879-0003electronic), 2019 Sep 15; 137: 1179-1189.
Impact Factor: 4.784
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Caterino M, Merlino A, Balsamo A, Russo Krauss I, Parisi S, Vergara A
* Reaction of Hg2+ Insertion into Cysteine Pairs Within Bovine Insulin Crystals Followed via Raman Spectroscopy (320 views)
J Solution Chem (ISSN: 0095-9782), 2014 Feb; 43(1): 135-143.
Impact Factor: 1.177
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Calce E, Sandomenico A, Saviano M, Ruvo M, De Luca S
* Cysteine Co-Oxidation Process Driven By Native Peptide Folding: An Example On Her2 Receptor Model System (371 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2014; 46(5): 1197-1206.
Impact Factor: 3.293
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Loguercio S, Dian C, Flagiello A, Scannella A, Pucci P, Terradot L, Zagari A
* In HspA from Helicobacter pylori vicinal disulfide bridges are a key determinant of domain B structure (247 views)
Febs Lett (ISSN: 0014-5793, 0014-5793print, 1873-3468electronic), 2008 Oct 15; 582(23-24): 3537-3541.
Impact Factor: 3.264
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Hilvo M, Baranauskiene L, Salzano AM, Scaloni A, Matulis D, Innocenti A, Scozzafava A, Monti SM, Di Fiore A, De Simone G, Lindfors M, Janis J, Valjakka J, Pastorekova S, Pastorek J, Kulomaa MS, Nordlund HR, Supuran CT, Parkkila S
* Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes (460 views)
Jbc Papers (ISSN: 0021-9258, 1083-351x, 0021-9258linking), 2008 Oct 10; 283(41): 27799-27809.
Impact Factor: 5.52
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Milardi D, Pappalardo M, Pannuzzo M, Grasso DM, Rosa CL
* The role of the Cys2-Cys7 disulfide bridge in the early steps of Islet amyloid polypeptide aggregation: A molecular dynamics study (447 views)
Chem Phys Lett (ISSN: 0009-2614), 2008 Oct 1; 463(4-6): 396-399.
Impact Factor: 2.169
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Dalla Serra M, Cirioni O, Vitale RM, Renzone G, Coraiola M, Giacometti A, Potrich C, Baroni E, Guella G, Sanseverino M, De Luca S, Scalise G, Amodeo P, Scaloni A
* Structural features of distinctin affecting peptide biological and biochemical properties (632 views)
Biochemistry (ISSN: 0006-2960, 1520-4995, 1520-4995electronic), 2008 Jul 29; 47(30): 7888-7899.
Impact Factor: 3.379
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De Simone A, Berisio R, Zagari A, Vitagliano L
* Limited Tendency Of Alpha-Helical Residues To Form Disulfide Bridges: A Structural Explanation (486 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2006 Dec; 12(12): 740-747.
Impact Factor: 1.801
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* Investigating the oxidative refolding mechanism of Cripto-1 CFC domain (321 views)
Int J Biol Macromol (ISSN: 0141-8130linking, 1879-0003electronic), 2019 Sep 15; 137: 1179-1189.
Impact Factor: 4.784
View Export to BibTeX Export to EndNote
Caterino M, Merlino A, Balsamo A, Russo Krauss I, Parisi S, Vergara A
* Reaction of Hg2+ Insertion into Cysteine Pairs Within Bovine Insulin Crystals Followed via Raman Spectroscopy (320 views)
J Solution Chem (ISSN: 0095-9782), 2014 Feb; 43(1): 135-143.
Impact Factor: 1.177
View Export to BibTeX Export to EndNote
Calce E, Sandomenico A, Saviano M, Ruvo M, De Luca S
* Cysteine Co-Oxidation Process Driven By Native Peptide Folding: An Example On Her2 Receptor Model System (371 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2014; 46(5): 1197-1206.
Impact Factor: 3.293
View Export to BibTeX Export to EndNote
Loguercio S, Dian C, Flagiello A, Scannella A, Pucci P, Terradot L, Zagari A
* In HspA from Helicobacter pylori vicinal disulfide bridges are a key determinant of domain B structure (247 views)
Febs Lett (ISSN: 0014-5793, 0014-5793print, 1873-3468electronic), 2008 Oct 15; 582(23-24): 3537-3541.
Impact Factor: 3.264
View Export to BibTeX Export to EndNote
Hilvo M, Baranauskiene L, Salzano AM, Scaloni A, Matulis D, Innocenti A, Scozzafava A, Monti SM, Di Fiore A, De Simone G, Lindfors M, Janis J, Valjakka J, Pastorekova S, Pastorek J, Kulomaa MS, Nordlund HR, Supuran CT, Parkkila S
* Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes (460 views)
Jbc Papers (ISSN: 0021-9258, 1083-351x, 0021-9258linking), 2008 Oct 10; 283(41): 27799-27809.
Impact Factor: 5.52
View Export to BibTeX Export to EndNote
Milardi D, Pappalardo M, Pannuzzo M, Grasso DM, Rosa CL
* The role of the Cys2-Cys7 disulfide bridge in the early steps of Islet amyloid polypeptide aggregation: A molecular dynamics study (447 views)
Chem Phys Lett (ISSN: 0009-2614), 2008 Oct 1; 463(4-6): 396-399.
Impact Factor: 2.169
View Export to BibTeX Export to EndNote
Dalla Serra M, Cirioni O, Vitale RM, Renzone G, Coraiola M, Giacometti A, Potrich C, Baroni E, Guella G, Sanseverino M, De Luca S, Scalise G, Amodeo P, Scaloni A
* Structural features of distinctin affecting peptide biological and biochemical properties (632 views)
Biochemistry (ISSN: 0006-2960, 1520-4995, 1520-4995electronic), 2008 Jul 29; 47(30): 7888-7899.
Impact Factor: 3.379
View Export to BibTeX Export to EndNote
De Simone A, Berisio R, Zagari A, Vitagliano L
* Limited Tendency Of Alpha-Helical Residues To Form Disulfide Bridges: A Structural Explanation (486 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2006 Dec; 12(12): 740-747.
Impact Factor: 1.801
View Export to BibTeX Export to EndNote
8 Records (8 excluding Abstracts).
Total impact factor: 25.387 (25.387 excluding Abstracts).
Total 5 year impact factor: 24.093 (24.093 excluding Abstracts).
Total impact factor: 25.387 (25.387 excluding Abstracts).
Total 5 year impact factor: 24.093 (24.093 excluding Abstracts).
604 views. Last view on Friday 02 June 2023, 8:17:54
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