Issue 91, 2014

Mammalian serum albumins as a chiral mediator library for bio-supramolecular photochirogenesis: optimizing enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate

Abstract

A simple strategy for choosing optimal bio-supramolecular mediators from the mammalian serum albumin library is proposed for bimolecular photochirogenic reactions. Thus, the enantiodifferentiating photocyclodimerization of 2-anthracencecarboxylate (AC) was optimized in chemical and optical yields, when mediated by porcine and canine serum albumins, both of which bound two AC molecules in the first productive site to give the (P)-enantiomer of syn-head-to-tail-cyclodimer in 69% yield and 89% enantiomeric excess (ee) for the former but the (M)-enantiomer in 77% yield and 97% ee for the latter.

Graphical abstract: Mammalian serum albumins as a chiral mediator library for bio-supramolecular photochirogenesis: optimizing enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate

Supplementary files

Article information

Article type
Communication
Submitted
24 Jun 2014
Accepted
22 Jul 2014
First published
22 Jul 2014

Chem. Commun., 2014,50, 14082-14085

Author version available

Mammalian serum albumins as a chiral mediator library for bio-supramolecular photochirogenesis: optimizing enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate

M. Nishijima, M. Goto, M. Fujikawa, C. Yang, T. Mori, T. Wada and Y. Inoue, Chem. Commun., 2014, 50, 14082 DOI: 10.1039/C4CC04818K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements