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Solid Phase Synthesis of Peptides and Glycopeptides on Polymeric Supports with Allylic Anchor Groups
Author(s) -
Kunz Horst,
Dombo Berthold
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198807111
Subject(s) - glycopeptide , chemistry , combinatorial chemistry , tyrosine , allylic rearrangement , peptide synthesis , peptide , amino acid , base (topology) , catalysis , solid phase synthesis , organic chemistry , biochemistry , mathematical analysis , mathematics , antibiotics
New polymeric supports (Hycram resins) have enabled the preparation of sensitive glycopeptides by solid‐phase synthesis . These resins make it possible to work with acid‐ and base‐labile protective groups, since the glycopeptides and peptides thus prepared can be recovered from the support by palladium(0) catalysis under neutral, weakly basic or weakly acid conditions. Acid(Boc)‐labile and base‐labile protective groups remain intact. Examples are the synthesis of the glycotripeptides 1b and of the Leu‐enkephalin 2b protected at the tyrosine via the Hycram compounds 1a and 1b .