Synthesis of GD3-lactam: a potential ligand for the development of an anti-melanoma vaccine

Carbohydrate Research
Nafizal HossainGöran Magnusson

Abstract

The novel sialyl donor methyl (ethyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-2-thio-3-thiophenyl-D-erythro-beta-L-gluco-non-2-ulopyranosid)onate was used for glycosylation of a lactosyl acceptor to give the GM3-trisaccharide derivative in 83% yield. Introduction of an azido group at C-9" of the GM3-trisaccharide derivative, transformation into a glycosyl acceptor, and sialylation with the above mentioned novel sialyl donor gave a GD3-trisaccharide in 50% yield. Reduction of the azido group gave the corresponding amine, which underwent spontaneous lactamization to the GD3-[1"'-9"]-lactam in an overall yield of 86%. Removal of protecting groups of over five steps, followed by per-O-acetylation gave an acetylated GD3-[1"'-9"]-lactam TMSEt glycoside in 27% overall yield. The acetylated GD3-[1"'-9"]-lactam TMSEt glycoside is suitable for glycosylation of linker-arms and the resulting linker-glycosides are planned to be coupled to carrier proteins, thus providing immunogens for trial vaccinations against malignant melanoma.

References

Oct 1, 1991·Current Opinion in Immunology·S Hakomori
Jul 15, 1994·International Journal of Cancer. Journal International Du Cancer·I KawashimaT Tai
Oct 1, 1995·Current Opinion in Structural Biology·K A Karlsson
Feb 1, 1997·Chemistry & Biology·S Hakomori, Y Zhang
Nov 14, 1997·Cancer Immunology, Immunotherapy : CII·P O Livingston, G Ragupathi
Mar 4, 2000·International Journal of Cancer. Journal International Du Cancer·G RagupathiP O Livingston

❮ Previous
Next ❯

Citations

Apr 6, 2011·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Sophie YacoubMagdi H Yacoub
Jul 7, 2018·Chemical Reviews·Carmanah D HunterChristopher W Cairo
Sep 11, 2004·The Journal of Organic Chemistry·Andréas Meijer, Ulf Ellervik

❮ Previous
Next ❯

Related Concepts

Related Feeds

Cardiac Glycosides

Cardiac glycosides are a diverse family of naturally derived compounds that bind to and inhibit na+/k+-atpase. Discover the latest research on cardiac glycosides heres.

Cancer Vaccines

Cancer vaccines are vaccines that either treat existing cancer or prevent development of a cancer.