Issue 7, 2012
From the journal:

RSC Advances

H-bonding promotion of peptide solubility and cyclization by fluorinated alcohols†

Hiroshi Hinou,*ab   Kei Hyugaji,a   Fayna Garcia-Martin,a   Shin-Ichiro Nishimuraa  and  Fernando Albericio*bc  

* Corresponding authors

a Graduate School of Life Science, and Frontier Research Center for Post-Genome Science and Technology, N21W11, Kita-ku, Sapporo, Japan
E-mail: hinou@sci.hokudai.ac.jp
Fax: 81 11 706 9042
Tel: 81 11 706 9040

b Institute for Research in Biomedicine (IRB), Barcelona Science Park (PCB) and CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, PCB Baldiri Reixac 10, Barcelona, Spain

c Department of Organic Chemistry, University of Barcelona, Martii Franques 1–11, Barcelona, Spain

Abstract

A promotion effect for peptide cyclization by strong H-bonding of fluorinated alcohols was revealed via a synthetic study of a cyclic AFGP skeleton. Combination of fluorinated alcohol-DCM solvent system and DIC-additive system afforded the cyclic hexapeptide skeleton in more than 80% yield. The ratio of intra- vs. inter-peptide condensation depended upon the H-bonding donor strength. This effect was quenched by H-bond acceptor solvents.

Graphical abstract: H-bonding promotion of peptide solubility and cyclization by fluorinated alcohols

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Article information

DOI
https://doi.org/10.1039/C2RA01043G
Article type
Communication
Submitted
07 Nov 2011
Accepted
17 Jan 2012
First published
27 Feb 2012

RSC Adv., 2012,2, 2729-2731

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H-bonding promotion of peptide solubility and cyclization by fluorinated alcohols

H. Hinou, K. Hyugaji, F. Garcia-Martin, S. Nishimura and F. Albericio, RSC Adv., 2012, 2, 2729 DOI: 10.1039/C2RA01043G

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