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An Improved Stereoselective Synthesis of L ‐Alanosine
Author(s) -
Strazzolini Paolo,
Dall’Arche Maria Grazia,
Zossi Maura,
Pavsler Andrea
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400508
Subject(s) - chemistry , stereoselectivity , alkylation , serine , substrate (aquarium) , yield (engineering) , amino acid , combinatorial chemistry , organic chemistry , biochemistry , enzyme , catalysis , ecology , materials science , metallurgy , biology
An improved, stereoselective synthesis of the natural, non‐proteogenic amino acid L ‐alanosine has been developed, starting from the readily available and cheap substrate L ‐serine, in six steps and 49% overall yield. The process is very efficient, is suitable for large‐scale production, and affords L ‐alanosine with properties comparable with those of the natural substance. In addition, the structural assignment concerning some previously reported synthetic alkylated derivatives of the natural amino acid has been definitively confirmed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)