Solid-state conformation of diastereomeric -Pro-Pro-(Aib)4 sequences

被引：18

作者：

Oba, Makoto ^{[2
]}

Demizu, Yosuke ^{[1
]}

Yamagata, Nanako ^{[1
]}

Sato, Yukiko ^{[1
]}

Doi, Mitsunobu ^{[3
]}

Tanaka, Masakazu ^{[4
]}

Suemune, Hiroshi ^{[2
]}

Okuda, Haruhiro ^{[1
]}

Kurihara, Masaaki ^{[1
]}

机构：

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

[2] Kyushu Univ, Grad Sch Pharmaceut Sci, Higashi Ku, Fukuoka 8128582, Japan

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

[4] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

TETRAHEDRON | 2010年 / 66卷 / 13期

关键词：

Peptide; Helix; X-ray crystallographic analysis; Conformation; Secondary structure; ALPHA-AMINO-ACIDS; CRYSTAL-STRUCTURE; DIPROLINE TEMPLATES; DESIGNED PEPTIDES; CHIRAL CENTERS; N-METHYLAMIDE; HAIRPIN; OLIGOPEPTIDES; 3(10)-HELIX; RESIDUES;

D O I：

10.1016/j.tet.2010.02.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The crystal structures of two diastereomeric -Pro-Pro-(Aib)(4)- sequences, CbZ-L-Pro-L-Pro-(Aib)(4)-OMe (1) and Cbz-D-Pro-L-Pro-(Aib)(4)-OMe (2), have been determined by X-ray crystallographic analysis. The crystals of the two compounds were characterized by the following parameters: (1) monochnic. P2(1), a=10.543 angstrom, b=8.103 angstrom, c=22.642 angstrom, beta=97.679, Z=2, R-1=0.104, and R-w=0.327: (2) orthorhombic, P2(1)2(1)2(1), a=10.470 angstrom, b=10.953 angstrom, c=32.405 angstrom, Z=4, R-1=0.040, and R-w=0.046. In the asymmetric Unit Of 1, the homochiral L-Pro(1)-L-Pro(2) adopts a polyproline II structure, which induces a left-handed (M) 3(10)-helical structure in the following -(Aib)(4)- sequence. The preferred conformation of diastereomeric 2, which contains heterochiral D-Pro(1)-L-Pro(2) segments, was similar to that of 1 with differences at the N-terminal D-Pro residue. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2293 / 2296

页数：4

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