The Bip method, based on the induced circular dichroism of a flexible biphenyl probe in terminally protected -Bip-Xaa*-dipeptides, for assignment of the absolute configuration of β-amino acids

被引：57

作者：

Dutot, Laurence ^{[1
]}

Wright, Karen ^{[1
]}

Gaucher, Anne ^{[1
]}

Wakselman, Michel ^{[1
]}

Mazaleyrat, Jean-Paul ^{[1
]}

De Zotti, Marta ^{[2
]}

Peggion, Cristina ^{[2
]}

Formaggio, Fernando ^{[2
]}

Toniolo, Claudio ^{[2
]}

机构：

[1] Univ Versailles, ILV, UMR 8180, CNRS, F-78035 Versailles, France

[2] Univ Padua, Dept Chem, CNR, Padova Unit, I-35131 Padua, Italy

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 18期

关键词：

D O I：

10.1021/ja800059d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An induced axial chirality of the biphenyl core of the Bip (2',1':1,2;1 '',2 '':3,4-dibenzcyclohepta-1,3-diene-6-amino-6-carboxylic acid) residue in the terminally protected dipeptides Boc-Bip-beta-Xaa*-OMe (beta-Xaa* = L-beta(3)-HAla, L-beta(3)-HVal, L-beta(3)-HLeu, L-beta(3)-HPro, trans-(1S,2S)-ACHC, trans-(1R,2R)-ACHC, trans(1S,2S)-ACPC, trans-(1R,2R)-ACPC) resulted in an induced circular dichroism, revealing the usefulness of the Bip method for a reliable and fast assignment of the absolute configuration of chiral beta-amino acids. Remarkably, the Bip method was also applied to the unique spin-labeled, cyclic, P-amino acids cis/trans-beta-TOAC and trans-POAC. In particular, this study allowed the assignment of the unknown absolute configurations of the enantiomers of the latter compound.

引用

页码：5986 / 5992

页数：7

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