Lipidated Peptides Via Post-Synthetic Thioalkylation Promoted By Molecular Sieves (479 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2014; 46(8): 1899-1905.
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Paper type: Journal Article,
Impact factor: 3.293, 5-year impact factor: 3.269
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84904755178&partnerID=40&md5=afc5736dff40098990e9075c761805c8
Keywords: Farnesylation, Lipidation, Molecular Sieves, Multi Derivatization, Peptide Thioalkylation, Lipidated Peptide, Peptide Derivative, Ras Protein, Unclassified Drug, Amino Acid Sequence, Analytical Equipment, Article, One Pot Synthesis, Priority Journal, Protein Processing, Protein Synthesis, Protein Thioalkylation,
Affiliations:
*** IBB - CNR ***
Institute of Biostructures and Bioimaging, National Research Council, 80134 Naples, Italy
Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309, United States
References:
Bader, B., Kuhn, K., Owen, D. J., Waldmann, H., Wittinghofer, A., Kuhlmann, J., Bioorganic synthesis of lipid-modified proteins for the study of signal transduction (2000) Nature, 403 (6766), pp. 223-226. , DOI 10. 1038/3500324
Bartels, C., Xia, T., Billeter, M., Gunthert, P., W thrich, K., The program XEASY for computer-supported NMR spectral analysis of biological macromolecules (1995) J Biomol NMR, 6, pp. 1-10
Bax, A., Davis, D. G., Practical aspects of two-dimensional transverse NOE spectroscopy (1985) J Magn Reson, 63, pp. 207-213
Berezovski, M., Li, W. -P., Poulter, C. D., Krylov, S. N., Measuring the activity of farnesyltransferase by capillary electrophoresis with laser-induced fluorescence detection (2002) Electrophoresis, 23 (19), pp. 3398-3403. , DOI 10. 1002/1522-2683 (200210) 23: 19<3398:: AID-ELPS3
Boguski, M. S., McCormick, F., Proteins regulating Ras and its relatives (1993) Nature, 366 (6456), pp. 643-654. , DOI 10. 1038/366643a0
Bourne, H. R., Sanders, D. A., McCormick, F., The GTPase superfamily: A conserved switch for diverse cell functions (1990) Nature, 348, pp. 125-132
Brown, M. J., Milano, P. D., Lever, D. C., Epstein, W. W., Poulter, C. D., Prenylated proteins. A convenient synthesis of farnesyl cysteinyl thioethers (1991) J Am Chem Soc, 113, pp. 3176-3177
Brunsveld, L., Kuhlmann, J., Alexandrov, K., Wittinghofer, A., Goody, R. S., Waldmann, H., Lipidated ras and rab peptides and proteins - Synthesis, structure, and function (2006) Angewandte Chemie - International Edition, 45 (40), pp. 6622-6646. , DOI 10. 1002/anie. 200600855
Calce, E., Leone, M., Monfregola, L., De Luca, S., Chemical modifications of peptide sequences via S-alkylation reaction (2013) Org Lett, 15, pp. 5354-5357
De Luca, S., Della, M. R., De Capua, A., Morelli, G., New synthetic strategy for o-NBS protected amino acids and their use in synthesis of mono-benzylated peptides (2005) Tetrahedron Letters, 46 (39), pp. 6637-6640. , DOI 10. 1016/j. tetlet. 2005. 07. 154, PII S0040403905016953
Gomashchi, F., Zhang, X. H., Liu, L., Gelb, M. H., Binding of prenylated and polybasic peptides to membranes - affinities and intervesicle exchange (1995) Biochemistry, 34, pp. 11910-11918
Griesinger, C., Otting, G., W thrich, K., Ernst, R. R., Clean TOCSY for 1H spin system identification in macromolecules (1988) J Am Chem Soc, 110, pp. 7870-7872
Hall, A., A biochemical function for ras - At last (1994) Science, 264, pp. 1413-1414. , and references therein
Hancock, J. F., Paterson, H., Marshall, C. J., A polybasic domain or palmitoylation is required in addition to the CAAX motif to localize p21ras to the plasma membrane (1990) Cell, 63, pp. 133-139
Lee, C. K., Vince, R., Effect of sparsomycin analogues on the puromycin-peptidyl transferase reaction on ribosomes (1978) Journal of Medicinal Chemistry, 21 (2), pp. 176-179
Lumbierres, M., Palomo, J. M., Kragol, G., Roehrs, S., Muller, O., Waldmann, H., Solid-phase synthesis of lipidated peptides (2005) Chemistry - A European Journal, 11 (24), pp. 7405-7415. , DOI 10. 1002/chem. 200500476
Monfregola, L., Leone, M., Calce, E., De Luca, S., Postsynthetic modification of peptides via chemoselective N-alkylation of their side chains (2012) Org Lett, 14, pp. 1664-1667
Mullen, D. G., Kyro, K., Hauser, M., Gustavsson, M., Veglia, G., Becker, J. M., Naider, F., Distefano, M. D., Synthesis of a-factor peptide from Saccharomyces cerevisiae and photoactive analogues via Fmoc solid phase methodology (2011) Bioorg Med Chem, 19, pp. 490-497
Naider, F. R., Becker, J. M., Synthesis of prenylated peptides and peptide esters (1997) Biopolymers, 43 (1), pp. 3-14
Okeley, N. M., Gelb, M. H., A designed probe for acidic phospholipids reveals the unique enriched anionic character of the cytosolic face of the mammalian plasma membrane (2004) Journal of Biological Chemistry, 279 (21), pp. 21833-21840. , DOI 10. 1074/jbc. M313469200
Perrey, D. A., Uckun, F. M., An improved method for cysteine alkylation (2001) Tetrahedron Letters, 42 (10), pp. 1859-1861. , DOI 10. 1016/S0040-4039 (01) 00098-3, PII S0040403901000983
Piantini, U., Sorensen, O. W., Ernst, R. R., Multiple quantum filters for elucidating NMR coupling networks (1982) J Am Chem Soc, 104, pp. 6800-6801
Triola, G., Brunsveld, L., Waldmann, H., Racemization-free synthesis of S-alkylated cysteines via thiol-ene reaction (2008) Journal of Organic Chemistry, 73 (9), pp. 3646-3649. , DOI 10. 1021/jo800198s
Vetter, I. R., Wittinghofer, A., The guanine nucleotide-binding switch in three dimensions (2001) Science, 294 (5545), pp. 1299-1304. , DOI 10. 1126/science. 1062023
Weise, K., Triola, G., Brunsveld, L., Waldmann, H., Winter, R., Influence of the lipidation motif on the partitioning and association of N-Ras in model membrane subdomains (2009) J Am Chem Soc, 131, pp. 1557-1564
Wright, T. M., Brooks, A. E. S., Didsbury, A. J., Williams, G. M., Harris, P. W. R., Dunbar, P. R., Brimble, M. A., Direct peptide lipidation through thiol-ene coupling enables rapid synthesis and evaluation of self-adjuvanting vaccine candidates (2013) Angew Chem Int Ed, 52, pp. 10616-10619
Xue, C. B., Becker, J. M., Naider, F., Efficient regioselective isoprenylation of peptides in acidic aqueous solution using zinc acetate as catalyst (1992) Tetrahedron Lett, 33, pp. 1435-1438
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2014; 46(8): 1899-1905.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 3.293, 5-year impact factor: 3.269
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84904755178&partnerID=40&md5=afc5736dff40098990e9075c761805c8
Keywords: Farnesylation, Lipidation, Molecular Sieves, Multi Derivatization, Peptide Thioalkylation, Lipidated Peptide, Peptide Derivative, Ras Protein, Unclassified Drug, Amino Acid Sequence, Analytical Equipment, Article, One Pot Synthesis, Priority Journal, Protein Processing, Protein Synthesis, Protein Thioalkylation,
Affiliations:
*** IBB - CNR ***
Institute of Biostructures and Bioimaging, National Research Council, 80134 Naples, Italy
Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309, United States
References:
Bader, B., Kuhn, K., Owen, D. J., Waldmann, H., Wittinghofer, A., Kuhlmann, J., Bioorganic synthesis of lipid-modified proteins for the study of signal transduction (2000) Nature, 403 (6766), pp. 223-226. , DOI 10. 1038/3500324
Bartels, C., Xia, T., Billeter, M., Gunthert, P., W thrich, K., The program XEASY for computer-supported NMR spectral analysis of biological macromolecules (1995) J Biomol NMR, 6, pp. 1-10
Bax, A., Davis, D. G., Practical aspects of two-dimensional transverse NOE spectroscopy (1985) J Magn Reson, 63, pp. 207-213
Berezovski, M., Li, W. -P., Poulter, C. D., Krylov, S. N., Measuring the activity of farnesyltransferase by capillary electrophoresis with laser-induced fluorescence detection (2002) Electrophoresis, 23 (19), pp. 3398-3403. , DOI 10. 1002/1522-2683 (200210) 23: 19<3398:: AID-ELPS3
Boguski, M. S., McCormick, F., Proteins regulating Ras and its relatives (1993) Nature, 366 (6456), pp. 643-654. , DOI 10. 1038/366643a0
Bourne, H. R., Sanders, D. A., McCormick, F., The GTPase superfamily: A conserved switch for diverse cell functions (1990) Nature, 348, pp. 125-132
Brown, M. J., Milano, P. D., Lever, D. C., Epstein, W. W., Poulter, C. D., Prenylated proteins. A convenient synthesis of farnesyl cysteinyl thioethers (1991) J Am Chem Soc, 113, pp. 3176-3177
Brunsveld, L., Kuhlmann, J., Alexandrov, K., Wittinghofer, A., Goody, R. S., Waldmann, H., Lipidated ras and rab peptides and proteins - Synthesis, structure, and function (2006) Angewandte Chemie - International Edition, 45 (40), pp. 6622-6646. , DOI 10. 1002/anie. 200600855
Calce, E., Leone, M., Monfregola, L., De Luca, S., Chemical modifications of peptide sequences via S-alkylation reaction (2013) Org Lett, 15, pp. 5354-5357
De Luca, S., Della, M. R., De Capua, A., Morelli, G., New synthetic strategy for o-NBS protected amino acids and their use in synthesis of mono-benzylated peptides (2005) Tetrahedron Letters, 46 (39), pp. 6637-6640. , DOI 10. 1016/j. tetlet. 2005. 07. 154, PII S0040403905016953
Gomashchi, F., Zhang, X. H., Liu, L., Gelb, M. H., Binding of prenylated and polybasic peptides to membranes - affinities and intervesicle exchange (1995) Biochemistry, 34, pp. 11910-11918
Griesinger, C., Otting, G., W thrich, K., Ernst, R. R., Clean TOCSY for 1H spin system identification in macromolecules (1988) J Am Chem Soc, 110, pp. 7870-7872
Hall, A., A biochemical function for ras - At last (1994) Science, 264, pp. 1413-1414. , and references therein
Hancock, J. F., Paterson, H., Marshall, C. J., A polybasic domain or palmitoylation is required in addition to the CAAX motif to localize p21ras to the plasma membrane (1990) Cell, 63, pp. 133-139
Lee, C. K., Vince, R., Effect of sparsomycin analogues on the puromycin-peptidyl transferase reaction on ribosomes (1978) Journal of Medicinal Chemistry, 21 (2), pp. 176-179
Lumbierres, M., Palomo, J. M., Kragol, G., Roehrs, S., Muller, O., Waldmann, H., Solid-phase synthesis of lipidated peptides (2005) Chemistry - A European Journal, 11 (24), pp. 7405-7415. , DOI 10. 1002/chem. 200500476
Monfregola, L., Leone, M., Calce, E., De Luca, S., Postsynthetic modification of peptides via chemoselective N-alkylation of their side chains (2012) Org Lett, 14, pp. 1664-1667
Mullen, D. G., Kyro, K., Hauser, M., Gustavsson, M., Veglia, G., Becker, J. M., Naider, F., Distefano, M. D., Synthesis of a-factor peptide from Saccharomyces cerevisiae and photoactive analogues via Fmoc solid phase methodology (2011) Bioorg Med Chem, 19, pp. 490-497
Naider, F. R., Becker, J. M., Synthesis of prenylated peptides and peptide esters (1997) Biopolymers, 43 (1), pp. 3-14
Okeley, N. M., Gelb, M. H., A designed probe for acidic phospholipids reveals the unique enriched anionic character of the cytosolic face of the mammalian plasma membrane (2004) Journal of Biological Chemistry, 279 (21), pp. 21833-21840. , DOI 10. 1074/jbc. M313469200
Perrey, D. A., Uckun, F. M., An improved method for cysteine alkylation (2001) Tetrahedron Letters, 42 (10), pp. 1859-1861. , DOI 10. 1016/S0040-4039 (01) 00098-3, PII S0040403901000983
Piantini, U., Sorensen, O. W., Ernst, R. R., Multiple quantum filters for elucidating NMR coupling networks (1982) J Am Chem Soc, 104, pp. 6800-6801
Triola, G., Brunsveld, L., Waldmann, H., Racemization-free synthesis of S-alkylated cysteines via thiol-ene reaction (2008) Journal of Organic Chemistry, 73 (9), pp. 3646-3649. , DOI 10. 1021/jo800198s
Vetter, I. R., Wittinghofer, A., The guanine nucleotide-binding switch in three dimensions (2001) Science, 294 (5545), pp. 1299-1304. , DOI 10. 1126/science. 1062023
Weise, K., Triola, G., Brunsveld, L., Waldmann, H., Winter, R., Influence of the lipidation motif on the partitioning and association of N-Ras in model membrane subdomains (2009) J Am Chem Soc, 131, pp. 1557-1564
Wright, T. M., Brooks, A. E. S., Didsbury, A. J., Williams, G. M., Harris, P. W. R., Dunbar, P. R., Brimble, M. A., Direct peptide lipidation through thiol-ene coupling enables rapid synthesis and evaluation of self-adjuvanting vaccine candidates (2013) Angew Chem Int Ed, 52, pp. 10616-10619
Xue, C. B., Becker, J. M., Naider, F., Efficient regioselective isoprenylation of peptides in acidic aqueous solution using zinc acetate as catalyst (1992) Tetrahedron Lett, 33, pp. 1435-1438
Lipidated Peptides Via Post-Synthetic Thioalkylation Promoted By Molecular Sieves
A thioalkylation procedure, which uses molecular sieves to promote the reaction, was exploited to provide peptides with useful functional groups (lipidic moieties), naturally occurring on proteins as post-translational modifications. The procedure was further implemented to synthesize tailor-made lipidated peptides, interesting tools to investigate biological processes involving their Ras parent proteins. Moreover, the one-pot preparation of multi-alkylated peptides confirms the versatility and flexibility of the employed methodology. 2014 Springer-Verlag
A thioalkylation procedure, which uses molecular sieves to promote the reaction, was exploited to provide peptides with useful functional groups (lipidic moieties), naturally occurring on proteins as post-translational modifications. The procedure was further implemented to synthesize tailor-made lipidated peptides, interesting tools to investigate biological processes involving their Ras parent proteins. Moreover, the one-pot preparation of multi-alkylated peptides confirms the versatility and flexibility of the employed methodology. 2014 Springer-Verlag
Lipidated Peptides Via Post-Synthetic Thioalkylation Promoted By Molecular Sieves
| ▼ Chemical modification of natural molecules, such as peptides and polysaccharides, to be employed as therapeutic agents as well as sensor diagnostic tools |
Lipidated Peptides Via Post-Synthetic Thioalkylation Promoted By Molecular Sieves
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7 Records (7 excluding Abstracts).
Total impact factor: 34.92 (34.92 excluding Abstracts).
Total 5 year impact factor: 25.597 (25.597 excluding Abstracts).
Total impact factor: 34.92 (34.92 excluding Abstracts).
Total 5 year impact factor: 25.597 (25.597 excluding Abstracts).
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