Chiral helicity induced by hydrogen bonding and chirality of podand histidyl moieties

被引：49

作者：

Moriuchi, T ^{[1
]}

Nishiyama, M ^{[1
]}

Yoshida, K ^{[1
]}

Ishikawa, T ^{[1
]}

Hirao, T ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 10期

关键词：

D O I：

10.1021/ol0100327

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The single-crystal X-ray structure determination of N,N ' -bis{(S)-(+)-1-methoxycarbonyl-2(4-imidazolyl)ethyl}-2,6-pyridinedicarboxamide (L-BHisPA) and the D-isomer (D-BHisPA) derived from the corresponding chiral histidine revealed a left- and right-handed helical conformation, respectively, through intramolecular hydrogen bonding and chirality of the podand histidyl moieties, Furthermore, each helical molecule is connected by continuous intermolecular hydrogen bonds to afford a left or right handed helical assembly, respectively, in the crystal packing.

引用

页码：1459 / 1461

页数：3

共 18 条

[11]

Kyte J.E., 2007, STRUCTURE PROTEIN CH, VSecond

[12] Intramolecular conformational control in ferrocenes bearing podand dipeptide chains [J].

Moriuchi, T ;

Nomoto, A ;

Yoshida, K ;

Hirao, T .

ORGANOMETALLICS, 2001, 20 (05) :1008-1013

[13] Characterization of ferrocene derivatives bearing podand dipeptide chains (-L-Ala-L-Pro-OR) [J].

Moriuchi, T ;

Nomoto, A ;

Yoshida, K ;

Hirao, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 589 (01) :50-58

[14] A highly ordered ferrocene system regulated by podand peptide chains [J].

Nomoto, A ;

Moriuchi, T ;

Yamazaki, S ;

Ogawa, A ;

Hirao, T .

CHEMICAL COMMUNICATIONS, 1998, (18) :1963-1964

[15]

NORIUCHI T, 2001, J AM CHEM SOC, V123, P68

[16]

Schulz G. E., 1979, PRINCIPLES PROTEIN S

[17] Synthesis and structure of chiral 2,6-bis[(2-carbamoyl-phenyl)carbamoyl]pyridine ligands [J].

Yu, Q ;

Baroni, TE ;

Liable-Sands, L ;

Rheingold, AL ;

Borovik, AS .

TETRAHEDRON LETTERS, 1998, 39 (38) :6831-6834

[18] Hydrogen bonded antiparallel β-strand motifs promoted by 2,6-bis(carbamoylpeptide)pyridine [J].

Yu, Q ;

Baroni, TE ;

Liable-Sands, L ;

Yap, GPA ;

Rheingold, AL ;

Borovik, AS .

CHEMICAL COMMUNICATIONS, 1999, (16) :1467-1468

← 1 2 →