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

Hossain, Nafizal; Zapata, Amparo; Wilstermann, Mikael; Nilsson, Ulf LU and Magnusson, Göran (2002) In Carbohydrate Research 337(7). p.569-580
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... (More)
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. (Less)
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Melanoma, Antigen, GD3, GD3-lactam, Glycosylation
in
Carbohydrate Research
volume
337
issue
7
pages
569 - 580
publisher
Elsevier
external identifiers
  • wos:000174862500001
  • pmid:11909589
  • scopus:0036129329
ISSN
1873-426X
DOI
10.1016/S0008-6215(02)00036-8
language
English
LU publication?
yes
id
e64f8053-1cca-43e7-ad36-7d374a706d57 (old id 105840)
date added to LUP
2007-07-10 11:17:19
date last changed
2017-04-30 06:24:24
@article{e64f8053-1cca-43e7-ad36-7d374a706d57,
  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.},
  author       = {Hossain, Nafizal and Zapata, Amparo and Wilstermann, Mikael and Nilsson, Ulf and Magnusson, Göran},
  issn         = {1873-426X},
  keyword      = {Melanoma,Antigen,GD3,GD3-lactam,Glycosylation},
  language     = {eng},
  number       = {7},
  pages        = {569--580},
  publisher    = {Elsevier},
  series       = {Carbohydrate Research},
  title        = {Synthesis of GD3-lactam: a potential ligand for the development of an anti-melanoma vaccine.},
  url          = {http://dx.doi.org/10.1016/S0008-6215(02)00036-8},
  volume       = {337},
  year         = {2002},
}