Synthesis of GD3-lactam: a potential ligand for the development of an anti-melanoma vaccine.
Författare
Summary, in English
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.
Avdelning/ar
Publiceringsår
2002
Språk
Engelska
Sidor
569-580
Publikation/Tidskrift/Serie
Carbohydrate Research
Volym
337
Issue
7
Dokumenttyp
Artikel i tidskrift
Förlag
Elsevier
Ämne
- Organic Chemistry
Nyckelord
- Melanoma
- Antigen
- GD3
- GD3-lactam
- Glycosylation
Status
Published
ISBN/ISSN/Övrigt
- ISSN: 1873-426X