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Multi-Step Synthesis and Biological Evaluation of Analogues of Insulin Secretagogue (2S,3R,4S)-4-Hydroxyisoleucine

✍ Scribed by Kaïss Aouadi; Anne-Dominique Lajoix; René Gross; Jean-Pierre Praly

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
440 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

A series of stereochemically defined analogues of (2__S__,3__R__,4__S__)‐4‐hydroxyisoleucine and related α‐hydroxy acids have been prepared by multi‐step routes from D‐glucose, whereas ketolization between TBDMS‐protected hydroxypropanone and ethyl isocyanoacetate led to racemic analogues. Bioassays showed that of eight newly synthesized compounds, two of them presented an interesting statistical trend to increase glucose‐induced insulin secretion when tested in isolated rat pancreatic islets in the presence of 8.3 mM glucose and at a concentration of 200 μM, which has previously been shown to be effective for (2__S__,3__R__,4__S__)‐4‐hydroxyisoleucine.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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