Oligosaccharides related to tumor-associated antigens. Part 3. Synthesis of the propyl glycosides of the trisaccharide β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp and of the tetrasaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp, components of a tumor antigen recognized by the antibody MBr1

L. Lay, L. Panza, G. Russo, D. Colombo, F. Ronchetti, E. Adobati, S. Canevari

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The synthesis of the trisaccharide β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp-1-OPr (2) and of the tetrasaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp-1-OPr (3), starting from the disaccharidic dihydrooxazole donor 5, is described. Glycosylation of 5 with 6 in the presence of Me3SiOTf gave the trisaccharide 7 which was deprotected with standard methods to give, via 8, compound 2. Alternatively, protection of 8 as the 4',6'-O-benzylidene derivative 9 followed by glycosylation with 10 and by standard deprotection afforded the tetrasaccharide 3. Biological testing showed that trisaccharide 2 is unable to inhibit the binding of the monoclonal antibody MBr1 to the target tumor cells MCF7, while tetrasaccharide 3 inhibits the binding in ca. 7-fold extent with respect to the previously tested trisaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-1-OPr. These results indicate that the galactose corresponding to the unit D of compound 1 plays an important role in defining the MBr1-recognized epitope and confirm the essential role of fucose for MAb recognition.

Original languageEnglish
Pages (from-to)533-538
Number of pages6
JournalHelvetica Chimica Acta
Volume78
Issue number3
DOIs
Publication statusPublished - 1995

Fingerprint

Glycosylation
Trisaccharides
Glycosides
Oligosaccharides
glucosides
Neoplasm Antigens
antigens
Antigens
antibodies
Antibodies
Tumors
tumors
Epitopes
galactose
Monoclonal antibodies
synthesis
Cells
Derivatives
Fucose
MCF-7 Cells

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

@article{8f76d602a0414fb09fa4537600315694,
title = "Oligosaccharides related to tumor-associated antigens. Part 3. Synthesis of the propyl glycosides of the trisaccharide β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp and of the tetrasaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp, components of a tumor antigen recognized by the antibody MBr1",
abstract = "The synthesis of the trisaccharide β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp-1-OPr (2) and of the tetrasaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp-1-OPr (3), starting from the disaccharidic dihydrooxazole donor 5, is described. Glycosylation of 5 with 6 in the presence of Me3SiOTf gave the trisaccharide 7 which was deprotected with standard methods to give, via 8, compound 2. Alternatively, protection of 8 as the 4',6'-O-benzylidene derivative 9 followed by glycosylation with 10 and by standard deprotection afforded the tetrasaccharide 3. Biological testing showed that trisaccharide 2 is unable to inhibit the binding of the monoclonal antibody MBr1 to the target tumor cells MCF7, while tetrasaccharide 3 inhibits the binding in ca. 7-fold extent with respect to the previously tested trisaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-1-OPr. These results indicate that the galactose corresponding to the unit D of compound 1 plays an important role in defining the MBr1-recognized epitope and confirm the essential role of fucose for MAb recognition.",
author = "L. Lay and L. Panza and G. Russo and D. Colombo and F. Ronchetti and E. Adobati and S. Canevari",
year = "1995",
doi = "10.1002/hlca.19950780302",
language = "English",
volume = "78",
pages = "533--538",
journal = "Helvetica Chimica Acta",
issn = "0018-019X",
publisher = "Verlag Helvetica Chimica Acta AG",
number = "3",

}

TY - JOUR

T1 - Oligosaccharides related to tumor-associated antigens. Part 3. Synthesis of the propyl glycosides of the trisaccharide β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp and of the tetrasaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp, components of a tumor antigen recognized by the antibody MBr1

AU - Lay, L.

AU - Panza, L.

AU - Russo, G.

AU - Colombo, D.

AU - Ronchetti, F.

AU - Adobati, E.

AU - Canevari, S.

PY - 1995

Y1 - 1995

N2 - The synthesis of the trisaccharide β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp-1-OPr (2) and of the tetrasaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp-1-OPr (3), starting from the disaccharidic dihydrooxazole donor 5, is described. Glycosylation of 5 with 6 in the presence of Me3SiOTf gave the trisaccharide 7 which was deprotected with standard methods to give, via 8, compound 2. Alternatively, protection of 8 as the 4',6'-O-benzylidene derivative 9 followed by glycosylation with 10 and by standard deprotection afforded the tetrasaccharide 3. Biological testing showed that trisaccharide 2 is unable to inhibit the binding of the monoclonal antibody MBr1 to the target tumor cells MCF7, while tetrasaccharide 3 inhibits the binding in ca. 7-fold extent with respect to the previously tested trisaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-1-OPr. These results indicate that the galactose corresponding to the unit D of compound 1 plays an important role in defining the MBr1-recognized epitope and confirm the essential role of fucose for MAb recognition.

AB - The synthesis of the trisaccharide β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp-1-OPr (2) and of the tetrasaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-(1 → 3)-α-D-Galp-1-OPr (3), starting from the disaccharidic dihydrooxazole donor 5, is described. Glycosylation of 5 with 6 in the presence of Me3SiOTf gave the trisaccharide 7 which was deprotected with standard methods to give, via 8, compound 2. Alternatively, protection of 8 as the 4',6'-O-benzylidene derivative 9 followed by glycosylation with 10 and by standard deprotection afforded the tetrasaccharide 3. Biological testing showed that trisaccharide 2 is unable to inhibit the binding of the monoclonal antibody MBr1 to the target tumor cells MCF7, while tetrasaccharide 3 inhibits the binding in ca. 7-fold extent with respect to the previously tested trisaccharide α-L-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-β-D-GalpNAc-1-OPr. These results indicate that the galactose corresponding to the unit D of compound 1 plays an important role in defining the MBr1-recognized epitope and confirm the essential role of fucose for MAb recognition.

UR - http://www.scopus.com/inward/record.url?scp=0029076022&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0029076022&partnerID=8YFLogxK

U2 - 10.1002/hlca.19950780302

DO - 10.1002/hlca.19950780302

M3 - Article

AN - SCOPUS:0029076022

VL - 78

SP - 533

EP - 538

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

SN - 0018-019X

IS - 3

ER -