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A New Convenient Route for the Synthesis of DOPA Peptides
Author(s) -
Nakonieczna Lucja,
Przychodzeń Witold,
Chimiak Andrzej
Publication year - 1994
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.199419941017
Subject(s) - chemistry , catechol , combinatorial chemistry , peptide , group (periodic table) , protecting group , terminal (telecommunication) , stereochemistry , organic chemistry , biochemistry , telecommunications , alkyl , computer science
Abstract The tert ‐butyldimethylsilyl group as the catechol protective group of DOPA (compound 1a ), Boc‐DOPA (compound 1b ) and DOPA esters (compounds 2a–c ) is introduced. The compounds 2a–c and 1b are used as the starting substrates for the synthesis of the protected N ‐terminal DOPA and C ‐terminal DOPA dipeptides, 3a–d and 4a–f , respectively. Optimal conditions for deprotection are presented. Acidolysis of the fully protected DOPA peptides 3a–d and 4a–f gives quantitatively the pure DOPA dipeptides in one step.