Helical Foldamer Containing a Combination of Cyclopentane-1,2-diamine and 2,2-Dimethylmalonic Acid

被引：8

作者：

Yamazaki, Norikazu ^{[1
]}

Demizu, Yosuke ^{[1
]}

Sato, Yukiko ^{[1
]}

Doi, Mitsunobu ^{[2
]}

Kurihara, Masaaki ^{[1
,3
]}

机构：

[1] Natl Inst Hlth Sci, Div Organ Chem, Tokyo 1588501, Japan

[2] Osaka Univ Pharmaceut Sci, Osaka 5691094, Japan

[3] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Yokohama, Kanagawa 2268501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 19期

基金：

日本学术振兴会;

关键词：

BETA-PEPTIDES; CRYSTALLOGRAPHIC CHARACTERIZATION; ALPHA/BETA-PEPTIDES; GAMMA-PEPTIDES; AMINO-ACIDS; DESIGN; OLIGOMERS; MIMICRY; GROWTH;

D O I：

10.1021/jo401505b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed new helical oligomers using a combination of (1S,2S)-cyclopentane-1,2-diamine [(S,S)-CPDA] and 2,2-dimethylmalonic acid (DMM) residues as building blocks. In solution, the preferred secondary structure of the (S,S) tetramer 6 was a right-handed (P) helix, and that of the (R,R) tetramer ent-6 was a left-handed (M) helix. In the crystalline state, both 6 and the (S,S) pentamer 7 folded into (P) 11-helices, and ent-6 folded into an (M) 11-helix with hydrogen bonds that were oriented in alternating directions.

引用

页码：9991 / 9994

页数：4

共 36 条

[1] Helical Structures of Bicyclic α-Amino Acid Homochiral Oligomers with the Stereogenic Centers at the Side-Chain Fused-Ring Junctions [J].

Anan, Kosuke ;

Demizu, Yosuke ;

Oba, Makoto ;

Kurihara, Masaaki ;

Doi, Mitsunobu ;

Suemune, Hiroshi ;

Tanaka, Masakazu .

HELVETICA CHIMICA ACTA, 2012, 95 (10) :1694-1713

[2] Polypeptide helices in hybrid peptide sequences [J].

Ananda, K ;

Vasudev, PG ;

Sengupta, A ;

Raja, KMP ;

Shamala, N ;

Balaram, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16668-16674

[3]

[Anonymous], CCDC946334

[4]

Beurskens P. T., 1994, DIRDIF 99 PROGRAM SY

[5] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[6] Crystallographic Characterization of the α/β-Peptide 14/15-Helix [J].

Choi, Soo Hyuk ;

Guzei, Ilia A. ;

Gellman, Samuel H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13780-+

[7] Peptide helices based on α-amino acids [J].

Crisma, M ;

Formaggio, F ;

Moretto, A ;

Toniolo, C .

BIOPOLYMERS, 2006, 84 (01) :3-12

[8] Surprisingly stable helical conformations in α/β-peptides by incorporation of cis-β-aminocyclopropane carboxylic acids [J].

De Pol, S ;

Zorn, C ;

Klein, CD ;

Zerbe, O ;

Reiser, O .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (04) :511-514

[9] One-Handed Helical Screw Direction of Homopeptide Foldamer Exclusively Induced by Cyclic α-Amino Acid Side-Chain Chiral Centers [J].

Demizu, Yosuke ;

Doi, Mitsunobu ;

Kurihara, Masaaki ;

Maruyama, Tokumi ;

Suemune, Hiroshi ;

Tanaka, Masakazu .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (08) :2430-2439

[10] Screw-Sense Control of Helical Oligopeptides Containing Equal Amounts of L- and D-Amino Acids [J].

Demizu, Yosuke ;

Doi, Mitsunobu ;

Sato, Yukiko ;

Tanaka, Masakazu ;

Okuda, Haruhiro ;

Kurihara, Masaaki .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (40) :11107-11109

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