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 beta-amino acids

Journal of the American Chemical Society
Laurence DutotClaudio Toniolo

Abstract

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, beta-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.

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Citations

Aug 25, 2015·Chirality·Keith W BentleyChristian Wolf
Jan 28, 2017·Journal of the American Chemical Society·Samantha L PilicerChristian Wolf
Sep 14, 2017·Chirality·Zeus A De Los SantosChristian Wolf
Oct 16, 2012·Chemical Communications : Chem Comm·Daniel P Iwaniuk, Christian Wolf
Jun 20, 2014·Organic & Biomolecular Chemistry·Hae-Geun JeonKyu-Sung Jeong
Mar 14, 2013·Chemical Society Reviews·Christian Wolf, Keith W Bentley
Nov 23, 2013·Journal of the American Chemical Society·Keith W BentleyChristian Wolf
Dec 7, 2013·Journal of the American Chemical Society·Mercy AnyikaBabak Borhan
Jun 18, 2014·The Journal of Organic Chemistry·Keith W Bentley, Christian Wolf
Jul 25, 2020·The Journal of Organic Chemistry·Samantha L PilicerChristian Wolf
Oct 1, 2019·Journal of the American Chemical Society·F Yushra ThanzeelChristian Wolf
Jan 30, 2009·Tetrahedron, Asymmetry·Carlos Cativiela, Mario Ordóñez

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