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Synthesis of Cyclosporine. I. Synthesis of enantiomerically pure (2 S ,3 R ,4 R ,6 E )‐3‐hydroxy ‐4‐methyl‐2‐methylamino‐6‐octenoic acid starting from tartaric acid
Author(s) -
Wenger Roland M.
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660742
Subject(s) - chemistry , stereospecificity , stereochemistry , tartaric acid , amino acid , strain (injury) , biochemistry , catalysis , medicine , citric acid
Starting from R , R ‐(+)‐tartaric acid, the synthesis of (2 S ,3 R ,4 R 6 E )‐3‐hydroxy ‐4‐methyl‐2‐methylamino‐6‐octenoic acid in 24 steps is reported. This novel amino acid is found in the cyclic undecapeptide cyclosporin A, isolated from the fungal strain Tolypocladium inflatum GAMS . Its stereospecific synthesis allowed, for the first time, the isolation and characterization of the new amino acid previously reported as the ‘C‐9‐amino acid’ [1].