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Lipidic Peptides, XIV. Conversion of Racemic Lipidic Amino Acids into Sphingosine and Ceramide Analogues and 1,2‐Diamines
Author(s) -
Kokotos George,
ConstantinouKokotou Violetta,
Fernandez Esther Del Olmo,
Toth Istvan,
Gibbons William A.
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1992199201158
Subject(s) - chemistry , ceramide , sphingosine , amino acid , stereochemistry , biochemistry , receptor , apoptosis
N ‐Protected racemic lipidic amino acids 1a – h were converted directly into ceramide analogues 2a – h by chemoselective reduction of their corresponding mixed anhydrides with sodium tetrahydroborate. Conversion of the compounds 1a , b into the corresponding acyl azides, followed by catalytic hydrogenation gave the N ‐monoprotected lipidic 1,2‐diamines 5a , b . The sphingosine analogues 7a – c and the free 1,2‐diamines 6a , b were synthesized by deprotection of the compounds 2a – c and 5a , b , respectively.