Efficient synthesis of both diastereomers of β,γ-diamino acids from phenylalanine and tryptophan

We synthesized in a few steps both diastereomers of orthogonally protected β,γ-diamino acids starting from l -phenylalanine or l -tryptophan. These final compounds are interesting building blocks for peptide synthesis and foldamer chemistry. The key step is a Blaise reaction performed under ultrasou...

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Bibliographic Details
Published in:	Amino acids Vol. 48; no. 9; pp. 2237 - 2242
Main Authors:	Auberger, Nicolas, Stanovych, Andrii, Thétiot-Laurent, Sophie, Guillot, Régis, Kouklovsky, Cyrille, Cote des Combes, Sylvain, Pacaud, Christophe, Devillers, Ingrid, Alezra, Valérie
Format:	Journal Article
Language:	English
Published:	Vienna Springer Vienna 01-09-2016 Springer Verlag
Subjects:	Analytical Chemistry Biochemical Engineering Biochemistry Biomedical and Life Sciences Chemical Sciences Life Sciences Neurobiology Original Article Phenylalanine - chemical synthesis Phenylalanine - chemistry Proteomics Stereoisomerism Tryptophan - chemical synthesis Tryptophan - chemistry Ultrasonic Waves β-amino acid Non proteinogenic amino acid synthesis Asymmetric synthesis γ-amino acid Blaise reaction
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Summary:	We synthesized in a few steps both diastereomers of orthogonally protected β,γ-diamino acids starting from l -phenylalanine or l -tryptophan. These final compounds are interesting building blocks for peptide synthesis and foldamer chemistry. The key step is a Blaise reaction performed under ultrasound conditions.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0939-4451 1438-2199
DOI:	10.1007/s00726-016-2262-8