NDLI: ß-Amino acids containing peptides and click-cyclized peptide as ß-turn mimics: a comparative study with 'conventional' lactam- and disulfide-bridged hexapeptides.

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ß-Amino acids containing peptides and click-cyclized peptide as ß-turn mimics: a comparative study with 'conventional' lactam- and disulfide-bridged hexapeptides.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Larregola, Maud Lequin, Olivier Karoyan, Philippe Guianvarc'h, Dominique Lavielle, Solange
Description	Country affiliation: France Author Affiliation: Larregola M ( UPMC Univ Paris, Laboratoire des BioMolécules, Place Jussieu, Boîte courrier, Paris, France.)
Abstract	The increasing interest in click chemistry and its use to stabilize turn structures led us to compare the propensity for ß-turn stabilization of different analogs designed as mimics of the ß-turn structure found in tendamistat. The ß-turn conformation of linear ß-amino acid-containing peptides and triazole-cyclized analogs were compared to 'conventional' lactam- and disulfide-bridged hexapeptide analogs. Their 3D structures and their propensity to fold in ß-turns in solution, and for those not structured in solution in the presence of -amylase, were analyzed by NMR spectroscopy and by restrained molecular dynamics with energy minimization. The linear tetrapeptide Ac-Ser-Trp-Arg-Tyr-NH(2) and both the amide bond-cyclized, c[Pro-Ser-Trp-Arg-Tyr-D-Ala] and the disulfide-bridged, Ac-c[Cys-Ser-Trp-Arg-Tyr-Cys]-NH(2) hexapeptides adopt dominantly in solution a ß-turn conformation closely related to the one observed in tendamistat. On the contrary, the ß-amino acid-containing peptides such as Ac-(R)-ß(3) -hSer-(S)-Trp-(S)-ß(3) -hArg-(S)-ß(3) -hTyr-NH(2) , and the triazole cyclic peptide, c[Lys-Ser-Trp-Arg-Tyr-ßtA]-NH(2) , both specifically designed to mimic this ß-turn, do not adopt stable structures in solution and do not show any characteristics of ß-turn conformation. However, these unstructured peptides specifically interact in the active site of -amylase, as shown by TrNOESY and saturation transfer difference NMR experiments performed in the presence of the enzyme, and are displaced by acarbose, a specific -amylase inhibitor. Thus, in contrast to amide-cyclized or disulfide-bridged hexapeptides, ß-amino acid-containing peptides and click-cyclized peptides may not be regarded as ß-turn stabilizers, but can be considered as potential ß-turn inducers.
File Format	HTM / HTML
ISSN	10752617
Issue Number	9
Volume Number	17
e-ISSN	10991387
Journal	Journal of Peptide Science
Language	English
Publisher	Wiley
Publisher Date	2011-09-01
Publisher Place	Great Britain (UK)
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Biochemistry Amino Acids Chemistry Disulfides Lactams Peptides Protein Structure, Secondary Amino Acid Sequence Cyclization Magnetic Resonance Spectroscopy Models, Molecular Molecular Sequence Data Molecular Structure Chemical Synthesis Genetics Journal Article
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Structural Biology Medicine Drug Discovery Biochemistry Molecular Biology Pharmacology Molecular Medicine

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