A striking periodicity of the cis/trans isomerization of proline imide bonds in cyclic disulfide-bridged peptides

被引：33

作者：

Shi, T ^{[1
]}

Spain, SM ^{[1
]}

Rabenstein, DL ^{[1
]}

机构：

[1] Univ Calif Riverside, Dept Chem, Riverside, CA 92521 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 11期

关键词：

disulfide peptides; isomerization; NMR spectroscopy; peptides; proline;

D O I：

10.1002/anie.200503470

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Graph Presented) cis persists: The population of the cis conformation of the Cys-Pro imide bond of the cyclic disulfide form of peptides of the sequence Ac-Cys-Pro-(Xaa)m-Cys-NH2 (Xaa = Phe, Ala) ranges from 9.3 to 76.9% and shows a striking periodic dependence on the number of residues in the peptide. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1780 / 1783

页数：4

共 38 条

[31] Discovery of a highly selective and efficient reagent for formation of intramolecular disulfide bonds in peptides [J].

Shi, TS ;

Rabenstein, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (29) :6809-6815

[32] Structure-function analysis of a phage display-derived peptide that binds to insulin-like growth factor binding protein 1 [J].

Skelton, NJ ;

Chen, YM ;

Dubree, N ;

Quan, C ;

Jackson, DY ;

Cochran, A ;

Zobel, K ;

Deshayes, K ;

Baca, M ;

Pisabarro, MT ;

Lowman, HB .

BIOCHEMISTRY, 2001, 40 (29) :8487-8498

[33] NMR solution structures of δ-conotoxin EVIA from Conus ermineus that selectively acts on vertebrate neuronal Na+ channels [J].

Volpon, L ;

Lamthanh, H ;

Barbier, J ;

Gilles, N ;

Molgó, J ;

Ménez, A ;

Lancelin, JM .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (20) :21356-21366

[34] Discovery and characterization of a family of insecticidal neurotoxins with a rare vicinal disulfide bridge [J].

Wang X.-H. ;

Connor M. ;

Smith R. ;

Maciejewski M.W. ;

Howden M.E.H. ;

Nicholson G.M. ;

Christie M.J. ;

King G.F. .

Nature Structural Biology, 2000, 7 (6) :505-513

[35] NOVEL DISULFIDE-CONSTRAINED PENTAPEPTIDES AS MODELS FOR BETA-VIA TURNS IN PROTEINS [J].

WEISSHOFF, H ;

FROST, K ;

BRANDT, W ;

HENKLEIN, P ;

MUGGE, C ;

FROMMEL, C .

FEBS LETTERS, 1995, 372 (2-3) :203-209

[36] Small peptides as potent mimetics of the protein hormone erythropoietin [J].

Wrighton, NC ;

Farrell, FX ;

Chang, R ;

Kashyap, AK ;

Barbone, FP ;

Mulcahy, LS ;

Johnson, DL ;

Barrett, RW ;

Jolliffe, LK ;

Dower, WJ .

SCIENCE, 1996, 273 (5274) :458-463

[37] Interaction of the cyclic antimicrobial cationic peptide bactenecin with the outer and cytoplasmic membrane [J].

Wu, MH ;

Hancock, REW .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (01) :29-35

[38] Impact of azaproline on amide cis-trans isomerism: Conformational analyses and NMR studies of model peptides including TRH analogues [J].

Zhang, WJ ;

Berglund, A ;

Kao, JLF ;

Couty, JP ;

Gershengom, MC ;

Marshall, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1221-1235

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