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Efficient Synthesis of Differently Protected Lanthionines via β‐Bromoalanine Derivatives
Author(s) -
Zhu Xiangming,
Schmidt Richard R.
Publication year - 2003
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.200300336
Subject(s) - chemistry , thioether , protecting group , combinatorial chemistry , group (periodic table) , base (topology) , cysteine , organic chemistry , stereochemistry , alkyl , mathematical analysis , mathematics , enzyme
Lanthionines, thioether‐linked alanines, are readily available from differently protected β‐bromoalanine and cysteine derivatives under phase‐transfer conditions at pH 8.5. Racemisation or elimination of starting materials or products was not observed. Also base‐sensitive protecting groups, such as, for instance, the Fmoc group, were compatible with this procedure, thus conveniently permitting the synthesis of orthogonally protected lanthionines. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)