umu.sePublications
Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Synthesis of a C-glycoside analogue of β-D -galactosyl threonine
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
2003 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, no 6, 2506-2509 p.Article in journal (Refereed) Published
Abstract [en]

C-linked analogue of β-d-galactosylthreonine has been prepared from 2,3,4,6-tetra-O-benzyl-d-galactopyranolactone (1) in 14 steps. Three stereogenic centers were created during the synthesis, with the anomeric center of the C-glycoside being generated first by addition of a Grignard reagent to 1 and subsequent reduction of the intermediate hemiacetal with triethylsilane. The two stereogenic centers in the threonine moiety were both established by alkylation of Evans' chiral N-acyloxazolidinone enolates.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2003. Vol. 68, no 6, 2506-2509 p.
National Category
Inorganic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-4780DOI: 10.1021/jo026758dOAI: oai:DiVA.org:umu-4780DiVA: diva2:144018
Available from: 2005-11-03 Created: 2005-11-03 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Asymmetric Synthesis of C-Glycosylated Amino Acids: Incorporation in Collagen Glycopeptides and Evaluation in a Model for Rheumatoid Arthritis
Open this publication in new window or tab >>Asymmetric Synthesis of C-Glycosylated Amino Acids: Incorporation in Collagen Glycopeptides and Evaluation in a Model for Rheumatoid Arthritis
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis describes stereoselective syntheses of four amino acids, three of which are C-glycosidic analogues of glycosylated amino acids. The overall goal of the project was to probe the interactions between MHC molecules, glycopeptide antigens and T cell receptors, that are essential for development of collagen induced arthritis. Collagen induced arthritis is a frequently used mouse model for rheumatoid arthritis, an autoimmune disease that attacks joint cartilage and leads to a painful and eventually crippling condition.

The thesis is based on four studies. The first study describes the synthesis of hydroxylysine, an amino acid that is found in collagen and is an important constituent of the glycopeptide proposed as an antigen in collagen induced arthritis. During the synthesis of hydroxylysine some new insight into the mechanism of the reductive opening of p-methoxybenzylidene acetals was obtained.

The remaining three studies deals with the synthesis of C-glycosidic analogues of glycosylated amino acids, hydroxy norvaline, threonine and hydroxylysine.The synthesis of each amino acid required control of several stereogenic centra and utilizes a variety of approaches such as use of stereoselective reactions, chiral auxilaries, chiral templates and asymmetric catalysis.

The C-glycosidic analogues of galactosylated hydroxynorvaline and hydroxylysine were incorporated in glycopeptides from type II collagen and evaluated in T cell response assays. It was found that the T cells were stimulated by the C-glycopeptides, but that higher concentrations were required than for the native O-glycopeptide

Place, publisher, year, edition, pages
Umeå: Kemi, 2005. 93 p.
Keyword
Total synthesis, stereoselective synthesis, chiral glycine templates, Evan’s alkylation, asymmetric hydrogenation, alpha-amino acid synthesis, C-glycoside, rheumatoid arthritis, MHC, T cell
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-623 (URN)91-7305-975-7 (ISBN)
Public defence
2005-11-25, 13:00
Supervisors
Available from: 2005-11-03 Created: 2005-11-03 Last updated: 2012-05-23Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Gustafsson, TomasSaxin, MariaKihlberg, Jan
By organisation
Department of Chemistry
In the same journal
Journal of Organic Chemistry
Inorganic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 89 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf