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Synthesis of Aib- and Phe(2Me)-Containing Cyclopentapeptides


Arnhold, Franziska S; Linden, Anthony; Heimgartner, Heinz (2015). Synthesis of Aib- and Phe(2Me)-Containing Cyclopentapeptides. Helvetica Chimica Acta, 98(2):155-178.

Abstract

Some recently described pentapeptides containing the alpha,alpha-disubstituted alpha-amino acids Aib and Phe(2Me) have been cyclized in DMF solution using diphenyl phosphorazidate (DPPA), O-(1H-benzotriazol-1-yl)-N,N,N’,N’-tetamethyluronium tetrafluoroborate/1-hydroxybenzotriazole (TBTU/HOBt), and diethyl phosphorocyanidate (DEPC), respectively, to give the corresponding cyclopentapeptides in fair-to-good yields. In the case of peptides with L-amino acids, and (R)- and (S)-Phe(2Me), the yields differed significantly in favor of the L/(R) combination. The conformations in the crystals of cyclo(Gly-Aib-(R,S)-Phe(2Me)-Aib-Gly) and cyclo(Gly-(R)-Phe(2Me)-Pro-Aib-Gly) have been determined by X-ray crystallography, leading to quite different results. In the latter case, the conformation in solution has been elucidated by NMR studies.

Abstract

Some recently described pentapeptides containing the alpha,alpha-disubstituted alpha-amino acids Aib and Phe(2Me) have been cyclized in DMF solution using diphenyl phosphorazidate (DPPA), O-(1H-benzotriazol-1-yl)-N,N,N’,N’-tetamethyluronium tetrafluoroborate/1-hydroxybenzotriazole (TBTU/HOBt), and diethyl phosphorocyanidate (DEPC), respectively, to give the corresponding cyclopentapeptides in fair-to-good yields. In the case of peptides with L-amino acids, and (R)- and (S)-Phe(2Me), the yields differed significantly in favor of the L/(R) combination. The conformations in the crystals of cyclo(Gly-Aib-(R,S)-Phe(2Me)-Aib-Gly) and cyclo(Gly-(R)-Phe(2Me)-Pro-Aib-Gly) have been determined by X-ray crystallography, leading to quite different results. In the latter case, the conformation in solution has been elucidated by NMR studies.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:February 2015
Deposited On:12 Mar 2015 10:28
Last Modified:15 Dec 2017 04:54
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Stipendienfonds der Basler Chemischen Industrie, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.201400323

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