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Solid‐Phase Synthesis of Cyclic C ‐Glycoside/Amino Acid Hybrids by Carbamate Coupling Chemistry and On‐Support Cyclization
Author(s) -
Katajisto Johanna,
Lönnberg Harri
Publication year - 2005
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.200500273
Subject(s) - chemistry , methoxide , glycoside , carbamate , solid phase synthesis , methanol , linker , organic chemistry , amino acid , polymer chemistry , combinatorial chemistry , peptide , biochemistry , computer science , operating system
Abstract A solid‐supported synthesis of cyclic C ‐glycoside/amino acid conjugates is described. For this purpose, N ‐( tert ‐butoxycarbonyl)‐[6‐ O ‐( p ‐nitrophenoxycarbonyl)‐2,3,4‐tri‐ O ‐( p ‐toluoyl)‐β‐ D ‐glycopyranosyl]methylamines derived from galactose and glucose were prepared and used as activated monomers together with appropriately protected amino acids. The solid phase assembly of the linear precursor was conducted by alternating peptide and carbamate coupling, using glutamate immobilized through its γ‐carboxy function to a SCAL linker as a handle. On‐support cyclization followed by cleavage from the support gave the desired conjugates. Removal of the p ‐toluoyl protections was carried out in solution phase by methoxide ion‐catalyzed transesterification in methanol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)