Conformational preferences of Ac-Gly-NHMe in solution

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Date

2015

Abstract

The conformational behaviour of Ac-Gly-NHMe in nonpolar, polar and polar protic solutions was systematically studied in this work by theoretical calculations and experimental infrared and 1H NMR spectroscopies. Ac-Gly-NHMe prefers a gauche conformer with a strong seven-membered intramolecular hydrogen bond for the isolated compound and in nonpolar solvents, but such preference changes in polar and polar protic solvents. Elucidation of Ac-Gly-NHMe preferences was also supported by studying the conformers of its CF3-C(O)-Gly-NHMe and Ac-Gly-N(Me)2 derivatives in solution.

Citation

Cormanich , R A , Rittner , R & Buehl , M 2015 , ' Conformational preferences of Ac-Gly-NHMe in solution ' RSC Advances , vol 5 , no. 16 , pp. 13052-13060 . DOI: 10.1039/C4RA16472E

Publication

RSC Advances

Status

Peer reviewed

DOI

http://dx.doi.org/10.1039/C4RA16472E

ISSN

2046-2069

Type

Journal article

Rights

© Royal Society of Chemistry 2015. No further copies may be made or distributed. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at http://dx.doi.org/10.1039/C4RA16472E

Description

The authors thank a Grant # 2012/03933-5, São Paulo Research Foundation (FAPESP) for providing financial support for this research and a scholarship to RAC #2011/01170-1 (FAPESP). CNPq is also acknowledged, such as for fellowships (to RR) and a studentship (to RAC).

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URI

http://hdl.handle.net/10023/8010

St Andrews Research Repository