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Synthesis of Constrained Peptidomimetics Containing 2-Oxo-1,3-oxazolidine-4-carboxylic Acids

✍ Scribed by Luca Gentilucci; Alessandra Tolomelli; Rossella De Marco; Claudia Tomasini; Sören Feddersen

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
255 KB
Volume
2011
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Sulfonyl peptides containing a serine or threonine residue undergo cyclization with bis(succinimidyl) carbonate (DSC) and diisopropylethylamine (DIPEA) to give peptides with a 2‐oxo‐1,3‐oxazolidine‐4‐carboxylate (Oxd) group, either in solution or in the solid phase. The position of the serine or threonine residue in the sequence is relatively unimportant. Under the same conditions, the corresponding Fmoc‐ or Boc‐peptides gave dehydration products, in agreement to previous studies. The protocol constitutes a valuable approach to the preparation of oxazolidinone‐containing peptides, which are a recently emerging class of constrained peptidomimetics. As a representative example, an Oxd analogue of the endogenous opioid peptide endomorphin‐1, characterized by an all‐trans conformation, was readily prepared.

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