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Issue 18, 2019
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Pyrrolidine ring puckering and prolyl amide bond configurations of 2-methyl-allo-hydroxyproline-based dipeptides

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Abstract

An expeditious method for the synthesis of homo and heterochiral dipeptides containing L-alanine and D/L 2-methyl allo-hydroxyl prolines was developed using direct aminolysis of bicyclic lactones derived from D/L alanine. The impact of C-2 methylation and its spatial orientation on the pyrrolidine ring puckering and prolyl amide bond configuration was ascertained by solution NMR studies. The present studies reveal that C-2 methylation causes the prolyl amide bond to exist exclusively in the trans geometry in both homo- and heterochiral dipeptides. However, the spatial orientation of the C-2 methyl group and its i + 2 position in appropriately capped model dipeptides may nucleate into a turn like structure.

Graphical abstract: Pyrrolidine ring puckering and prolyl amide bond configurations of 2-methyl-allo-hydroxyproline-based dipeptides

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Article information


Submitted
19 Jan 2019
Accepted
04 Apr 2019
First published
04 Apr 2019

Org. Biomol. Chem., 2019,17, 4460-4464
Article type
Communication

Pyrrolidine ring puckering and prolyl amide bond configurations of 2-methyl-allo-hydroxyproline-based dipeptides

V. S. Tiwari, G. Singh, Gurudayal, R. S. Ampapathi and W. Haq, Org. Biomol. Chem., 2019, 17, 4460
DOI: 10.1039/C9OB00150F

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