Folding of peptides characterized by c3Val, a highly constrained analogue of valine (465 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2003; 68(2): 178-191.
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Paper type: Journal Article,
Impact factor: 2.733, 5-year impact factor: 2.675
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0037322818&partnerID=40&md5=af126fd9069374b33e779f5ff32d2eb1
Keywords: β-Bend, 310-Helix, Amino Acid Synthesis, Cα-Tetrasubstituted α-Amino Acids, Conformational Analysis, Cyclopropane Amino Acid, Ir Absorption, Peptide Synthesis, X-Ray Diffraction, Fourier Transform Infrared Spectroscopy, Synthesis (chemical), X Ray Diffraction, Chirality, Amino Acid Derivative, Glycine, Valine, Article, Biosynthesis, Crystal Structure, Enantiomer, Intermethod Comparison, Methylation, Protein Analysis, Protein Folding, Protein Structure, Crystallography, Models, Molecular, Molecular Conformation, Oligopeptides, Protein Conformation, ß-Bend, Ca-Tetrasubstituted A-Amino Acids,
Affiliations:
*** IBB - CNR ***
Institute of Biomolecular Chemistry, Department of Organic Chemistry, University of Padova, 35131 Padova, Italy
DSM Fine Chemicals, Advanced Synthesis and Catalysis, P. O. Box 18, 6160 MD Geleen, Netherlands
Inst. of Biostructures/Bioimaging, Department of Chemistry, University of Naples Federico II, 80134 Naples, Italy
References:
Not available.
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2003; 68(2): 178-191.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 2.733, 5-year impact factor: 2.675
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0037322818&partnerID=40&md5=af126fd9069374b33e779f5ff32d2eb1
Keywords: β-Bend, 310-Helix, Amino Acid Synthesis, Cα-Tetrasubstituted α-Amino Acids, Conformational Analysis, Cyclopropane Amino Acid, Ir Absorption, Peptide Synthesis, X-Ray Diffraction, Fourier Transform Infrared Spectroscopy, Synthesis (chemical), X Ray Diffraction, Chirality, Amino Acid Derivative, Glycine, Valine, Article, Biosynthesis, Crystal Structure, Enantiomer, Intermethod Comparison, Methylation, Protein Analysis, Protein Folding, Protein Structure, Crystallography, Models, Molecular, Molecular Conformation, Oligopeptides, Protein Conformation, ß-Bend, Ca-Tetrasubstituted A-Amino Acids,
Affiliations:
*** IBB - CNR ***
Institute of Biomolecular Chemistry, Department of Organic Chemistry, University of Padova, 35131 Padova, Italy
DSM Fine Chemicals, Advanced Synthesis and Catalysis, P. O. Box 18, 6160 MD Geleen, Netherlands
Inst. of Biostructures/Bioimaging, Department of Chemistry, University of Naples Federico II, 80134 Naples, Italy
References:
Not available.
Folding of peptides characterized by c3Val, a highly constrained analogue of valine
Using a combined chemical/chiral chromatographic approach we synthesized an N-protected derivative of (R)-c3Val, a severely conformationally restricted Cα-tetrasubstituted α-amino acid characterized by a Cβ,β-dimethylated cyclopropane system. A set of terminally protected derivatives and model peptides (to the heptamer level), containing one or two (R)-c3Val residues in combination with either Aib or Gly residues, was prepared by solution methods. A detailed solution and crystal-state conformational investigation, based on Fourier transform infrared (FTIR) absorption, 1H-NMR, and x-ray diffraction techniques, performed in comparison with a similar study on related derivatives and peptides rich in (αMe)Val, the prototype of Cα-tetrasubstituted α-amino acids of this subfamily, allowed us to conclude the following: (a) c3Val is a good β-bend and helix former, although less efficient than (αMe)Val. (b) The relationship between α-carbon chirality and screw sense of the folded structure formed is the same as that of (αMe)Val, i.e., the (R)-enantiomer has a strong left-handed bias. (c) c3Val seems more prone than (αMe)Val to fold into a γ-bend conformation. The conformational propensities of Cβ,β-disubstituted Ac3c residues are also discussed in comparison with those of the parent cyclopropane residue. © 2002 Wiley Periodicals, Inc.
Using a combined chemical/chiral chromatographic approach we synthesized an N-protected derivative of (R)-c3Val, a severely conformationally restricted Cα-tetrasubstituted α-amino acid characterized by a Cβ,β-dimethylated cyclopropane system. A set of terminally protected derivatives and model peptides (to the heptamer level), containing one or two (R)-c3Val residues in combination with either Aib or Gly residues, was prepared by solution methods. A detailed solution and crystal-state conformational investigation, based on Fourier transform infrared (FTIR) absorption, 1H-NMR, and x-ray diffraction techniques, performed in comparison with a similar study on related derivatives and peptides rich in (αMe)Val, the prototype of Cα-tetrasubstituted α-amino acids of this subfamily, allowed us to conclude the following: (a) c3Val is a good β-bend and helix former, although less efficient than (αMe)Val. (b) The relationship between α-carbon chirality and screw sense of the folded structure formed is the same as that of (αMe)Val, i.e., the (R)-enantiomer has a strong left-handed bias. (c) c3Val seems more prone than (αMe)Val to fold into a γ-bend conformation. The conformational propensities of Cβ,β-disubstituted Ac3c residues are also discussed in comparison with those of the parent cyclopropane residue. © 2002 Wiley Periodicals, Inc.
Folding of peptides characterized by c3Val, a highly constrained analogue of valine
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Folding of peptides characterized by c3Val, a highly constrained analogue of valine
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View Export to BibTeX Export to EndNote
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View Export to BibTeX Export to EndNote
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View Export to BibTeX Export to EndNote
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Impact Factor: 3.432
View Export to BibTeX Export to EndNote
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View Export to BibTeX Export to EndNote
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View Export to BibTeX Export to EndNote
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View Export to BibTeX Export to EndNote
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Impact Factor: 4.773
View Export to BibTeX Export to EndNote
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Impact Factor: 4.106
View Export to BibTeX Export to EndNote
Roviello GN, Gröschel S, Pedone C, Diederichsen U
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Amino Acids (ISSN: 1438-2199, 0939-4451, 1438-2199electronic), 2010 May; 38(5): 1301-1309.
Impact Factor: 4.106
View Export to BibTeX Export to EndNote
Roviello GN, Musumeci D, Moccia M, Castiglione M, Cesarani A, Bucci EM, Saviano M, Pedone C, Benedetti E
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Impact Factor: 1.807
View Export to BibTeX Export to EndNote
Calvanese L, Saporito A, Oliva R, D'Auria G, Pedone C, Paolillo L, Ruvo M, Marasco D, Falcigno L
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Impact Factor: 1.807
View Export to BibTeX Export to EndNote
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Impact Factor: 1.807
View Export to BibTeX Export to EndNote
Merlino A, Vergara A, Sica F, Mazzarella L
* The bis-histidyl complex in hemoproteins: A detailed conformational analysis of database protein structures and the case of Antarctic fish hemoglobins (340 views)
Marine Genomics (ISSN: 1874-7787), 2009 Mar; 2(1): 51-56.
Impact Factor: 1.2
View Export to BibTeX Export to EndNote
Di Gaetano S, Guglielmi F, Arciello A, Mangione P, Monti M, Pagnozzi D, Raimondi S, Giorgetti S, Orru S, Canale C, Pucci P, Dobson CM, Bellotti V, Piccoli R
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Impact Factor: 2.855
View Export to BibTeX Export to EndNote
Vacatello M, D'Auria G, Falcigno L, Dettin M, Gambaretto R, Di Bello C, Paolillo L
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Impact Factor: 4.698
View Export to BibTeX Export to EndNote
Saviano M, Isernia C, Bassarello C, Di Lello P, Galdiero S, Mierke DF, Benedetti E, Pedone C
* Conformational analysis by NMR and distance geometry techniques of a peptide mimetic of the third helix of the Antennapedia homeodomain (506 views)
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Impact Factor: 1.741
View Export to BibTeX Export to EndNote
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Impact Factor: 2.931
View Export to BibTeX Export to EndNote
Romanelli A, Garella I, Menchise V, Iacovino R, Saviano M, Montesarchio D, Didierjean C, Lello PD, Rossi F, Benedetti E
* Crystal-state conformation of Cα, α-dialkylated peptides containing chiral β-homo-residues (539 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2001; 7(1): 15-26.
Impact Factor: 1.451
View Export to BibTeX Export to EndNote
Crisma M, Formaggio F, Valle G, Toniolo C, Saviano M, Iacovino R, Zaccaro L, Benedetti E
Experimental evidence at atomic resolution for intramolecular N- H···π (phenyl) interactions in a family of amino acid derivatives (436 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1997; 42(1): 1-6.
Impact Factor: 2.425
View Export to BibTeX Export to EndNote
Zanotti G, Maione A, Rossi F, Saviano M, Pedone C, Tancredi T
BIOACTIVE PEPTIDES - CONFORMATIONAL STUDY OF A CYSTINYL CYCLOHEPTAPEPTIDE IN ITS FREE AND CALCIUM COMPLEXED FORMS (593 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 1993 Jul; 33(7): 1083-1091.
Impact Factor: 2.425
View Export to BibTeX Export to EndNote
22 Records (22 excluding Abstracts).
Total impact factor: 65.332 (65.332 excluding Abstracts).
Total 5 year impact factor: 71.452 (71.452 excluding Abstracts).
Total impact factor: 65.332 (65.332 excluding Abstracts).
Total 5 year impact factor: 71.452 (71.452 excluding Abstracts).
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