The synthesis of the trisaccharide alpha-L-Fucp-(1-->2)-beta-D-Galp-(1-->3)-beta-D-GalpNAc-1-OPr (2) is described. The N-acetylgalactosamine 6 was obtained from 4 by an intramolecular displacement of a (trifluoromethyl)sulfonyloxy by a pivaloyloxy group with its concomitant migration from position 3 to position 4 (Scheme 1). The galactosyl donor 9 was obtained from 7 via 8 by regioselective opening of the orthoester function with AcOH/pyridine followed by treatment with CCl3CN and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (Scheme 2). Glycosylation of 6 with 9 in the presence of BF3.OEt2 gave the disaccharide 10. Selective deprotection of 10 at O -C(2') followed by glycosylation with 12 and by standard deprotection afforded the title trisaccharide 2 (Scheme 3). Preliminary biological testing showed that 2 is able to inhibit the binding of the monoclonal antibody MBr1 to the target tumor celles MCF7 in a dose-dependent manner.
Oligosaccharides Related to Tumor-Associated Antigens. Part I. Synthesis of the propyl glycoside of the trisaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc, component of a tumor antigen recognized by the antibody MBr1 / L. Lay, F. Nicotra, L. Panza, G. Russo, E. Adobati. - In: HELVETICA CHIMICA ACTA. - ISSN 0018-019X. - 77:2(1994), pp. 509-514.
|Titolo:||Oligosaccharides Related to Tumor-Associated Antigens. Part I. Synthesis of the propyl glycoside of the trisaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc, component of a tumor antigen recognized by the antibody MBr1|
LAY, LUIGI (Primo)
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||1994|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1002/hlca.19940770211|
|Appare nelle tipologie:||01 - Articolo su periodico|