Stabilisation of Peptide Foldamers in an Aqueous Medium by Incorporation of Azapeptide Building Blocks

被引：30

作者：

Hetenyi, Anasztazia ^{[1
,2
]}

Toth, Gabor K. ^{[2
]}

Somlai, Csaba ^{[2
]}

Vass, Elemer ^{[3
]}

Martinek, Tamas A. ^{[1
]}

Fueloep, Ferenc ^{[1
]}

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary

[2] Univ Szeged, Dept Med Chem, H-6720 Szeged, Hungary

[3] Eotvos Lorand Univ, Inst Chem, H-1117 Budapest, Hungary

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 41期

关键词：

amino acids; chirality; foldamers; peptides; peptidomimetics; DE-NOVO DESIGN; BETA-PEPTIDE; SECONDARY STRUCTURE; CIRCULAR-DICHROISM; 14-HELIX STABILITY; AMINO-ACIDS; HELIX; NMR; AZA-BETA(3)-PEPTIDES; CONFORMATION;

D O I：

10.1002/chem.200900724

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stable foldamers in water: Helical peptidic foldamers including H12 and H10/12 helices were constructed and stabilised in water. The foldamers' extra rigidity stems from the strong hydrogen bonding network of the azapeptide groups (see graphic). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：10736 / 10741

页数：6

共 54 条

[1] NMR method for the determination of solute hydrogen bond acidity [J].

Abraham, MH ;

Abraham, RJ ;

Byrne, J ;

Griffiths, L .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3389-3394

[2] Extracting information from the temperature gradients of polypeptide NH chemical shifts .1. The importance of conformational averaging [J].

Andersen, NH ;

Neidigh, JW ;

Harris, SM ;

Lee, GM ;

Liu, ZH ;

Tong, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (36) :8547-8561

[3] Residue-based control of helix shape in beta-peptide oligomers [J].

Appella, DH ;

Christianson, LA ;

Klein, DA ;

Powell, DR ;

Huang, XL ;

Barchi, JJ ;

Gellman, SH .

NATURE, 1997, 387 (6631) :381-384

[4] Antibiotic and hemolytic activity of a β2/β3 peptide capable of folding into a 12/10-helical secondary structure [J].

Arvidsson, PI ;

Ryder, NS ;

Weiss, HM ;

Gross, G ;

Kretz, O ;

Woessner, R ;

Seebach, D .

CHEMBIOCHEM, 2003, 4 (12) :1345-1347

[5] Design, machine synthesis, and NMR-solution structure of a β-heptapeptide forming a salt-bridge stabilised 314-helix in methanol and in water [J].

Arvidsson, PI ;

Rueping, M ;

Seebach, D .

CHEMICAL COMMUNICATIONS, 2001, (07) :649-650

[6] On the flexibility of β-peptides [J].

Beke, T ;

Csizmadia, IG ;

Perczel, A .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 2004, 25 (02) :285-307

[7] Solution synthesis and characterization of aza-β3-peptides (Nα-substituted hydrazino acetic acid oligomers) [J].

Cheguillaume, A ;

Salaün, A ;

Sinbandhit, S ;

Potel, M ;

Gall, P ;

Baudy-Floc'h, M ;

Le Grel, P .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4923-4929

[8] Long-range interactions stabilize the fold of a non-natural oligomer [J].

Cheng, RP ;

DeGrado, WF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11564-11565

[9] De novo design of a monomeric helical β-peptide stabilized by electrostatic interactions [J].

Cheng, RP ;

DeGrado, WF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (21) :5162-5163

[10] Rational development of β-peptide inhibitors of human cytomegalovirus entry [J].

English, EP ;

Chumanov, RS ;

Gellman, SH ;

Compton, T .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (05) :2661-2667

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