Synthesis of GD3-lactam: a potential ligand for the development of an anti-melanoma vaccine.
(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:
https://lup.lub.lu.se/record/105840
- author
- Hossain, Nafizal ; Zapata, Amparo ; Wilstermann, Mikael ; Nilsson, Ulf LU and Magnusson, Göran
- organization
- publishing date
- 2002
- 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
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- e64f8053-1cca-43e7-ad36-7d374a706d57 (old id 105840)
- date added to LUP
- 2016-04-01 11:33:33
- date last changed
- 2022-01-26 07:03:39
@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}},
keywords = {{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}},
doi = {{10.1016/S0008-6215(02)00036-8}},
volume = {{337}},
year = {{2002}},
}