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Synthesis of GD3-la...
Synthesis of GD3-lactam: a potential ligand for the development of an anti-melanoma vaccine.
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Hossain, Nafizal (författare)
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Zapata, Amparo (författare)
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Wilstermann, Mikael (författare)
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- Nilsson, Ulf (författare)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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Magnusson, Göran (författare)
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visa färre...
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(creator_code:org_t)
- 2002
- 2002
- Engelska.
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Ingår i: Carbohydrate Research. - 1873-426X. ; 337:7, s. 569-580
- Relaterad länk:
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http://dx.doi.org/10...
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https://lup.lub.lu.s...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- 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.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- Melanoma
- Antigen
- GD3
- GD3-lactam
- Glycosylation
Publikations- och innehållstyp
- art (ämneskategori)
- ref (ämneskategori)
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