Synthesis of a novel cis-proline-derived cyclic type VI β-turn mimic via ring-closing metathesis

被引：27

作者：

Boruah, A

Rao, IN

Nandy, JP

Kumar, SK

Kunwar, AC

Iqbal, J ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

[2] Dr Reddys Labs Ltd, Hyderabad 500050, Andhra Pradesh, India

[3] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 12期

关键词：

D O I：

10.1021/jo020618m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cis-proline derived cyclic mimic of a type VI beta-turn is synthesized via a ring-closing metathesis reaction. The solution NMR conformational study indicates that the major conformer of the cyclic peptide adopts a type VIA beta-turn in CDCl3 and a type VIb beta-turn in DMSO-d(6).

引用

页码：5006 / 5008

页数：3

共 31 条

[1] Molecular recognition of protein-ligand complexes: Applications to drug design
Babine, RE
Bender, SL
[J]. CHEMICAL REVIEWS, 1997, 97 (05) : 1359 - 1472
[2] Synthesis of a cyclic pseudo 310 helical structure from a β-amino acid-L-proline derived tripeptide via a ring closing metathesis reaction
Banerji, B
Mallesham, B
Kumar, SK
Kunwar, AC
Iqbal, J
[J]. TETRAHEDRON LETTERS, 2002, 43 (36) : 6479 - 6483
[3] Synthesis of cyclic β-turn mimics from L-Pro-Phe/Phe-L-Pro derived di- and tripeptides via ring closing metathesis:: the role of chirality of the Phe residue during cyclization
Banerji, B
Bhattacharya, M
Madhu, RB
Das, SK
Iqbal, J
[J]. TETRAHEDRON LETTERS, 2002, 43 (36) : 6473 - 6477
[4] EMPIRICAL PREDICTIONS OF PROTEIN CONFORMATION
CHOU, PY
FASMAN, GD
[J]. ANNUAL REVIEW OF BIOCHEMISTRY, 1978, 47 : 251 - 276
[5] CIAJOLO MR, 1992, BIOPOLYMERS, V32, P727
[6] THE HIV-1 PROTEASE AS A THERAPEUTIC TARGET FOR AIDS
DEBOUCK, C
[J]. AIDS RESEARCH AND HUMAN RETROVIRUSES, 1992, 8 (02) : 153 - 164
[7] PEPTIDYL-PROLYL CIS/TRANS ISOMERASES AND THEIR EFFECTORS
FISCHER, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (14) : 1415 - 1436
[8] MULTIPLE CONFORMATIONS OF A PROTEIN DEMONSTRATED BY MAGNETIZATION TRANSFER NMR-SPECTROSCOPY
FOX, RO
EVANS, PA
DOBSON, CM
[J]. NATURE, 1986, 320 (6058) : 192 - 194
[9] PREDICTION OF PROLYL RESIDUES IN CIS-CONFORMATION IN PROTEIN STRUCTURES ON THE BASIS OF THE AMINO-ACID-SEQUENCE
FROMMEL, C
PREISSNER, R
[J]. FEBS LETTERS, 1990, 277 (1-2) : 159 - 163
[10] Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

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