Synthesis of 2-alkoxy-8-hydroxyadenylpeptides: towards synthetic epitope-based vaccines

Jimmy J Weterings; Selina Khan; Gerbrand J van der Heden; Jan W Drijfhout; Cornelis J M Melief; Herman S Overkleeft; Sjoerd H van der Burg; Ferry Ossendorp; Gijsbert A van der Marel; Dmitri V Filippov

doi:10.1016/j.bmcl.2006.03.034

Synthesis of 2-alkoxy-8-hydroxyadenylpeptides: towards synthetic epitope-based vaccines

Bioorg Med Chem Lett. 2006 Jun 15;16(12):3258-61. doi: 10.1016/j.bmcl.2006.03.034. Epub 2006 Apr 11.

Authors

Jimmy J Weterings¹, Selina Khan, Gerbrand J van der Heden, Jan W Drijfhout, Cornelis J M Melief, Herman S Overkleeft, Sjoerd H van der Burg, Ferry Ossendorp, Gijsbert A van der Marel, Dmitri V Filippov

Affiliation

¹ Leiden Institute of Chemistry, Leiden University, PO Box 9502, 2300 RA Leiden, The Netherlands.

PMID: 16581248
DOI: 10.1016/j.bmcl.2006.03.034

Abstract

The preparation of three different 2-alkoxy-8-hydroxyadenylpeptide conjugates has been accomplished by solid-phase synthesis combined with 'on-resin' Cu(I) catalyzed Huisgen cycloaddition. The immunogenicity of the compounds has been evaluated in IL-12 production and antigen presentation assays.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenine / analogs & derivatives*
Adenine / chemistry
Antigen Presentation / immunology
Dendritic Cells / immunology
Epitopes / chemistry*
Epitopes / immunology*
Histocompatibility Antigens Class I / immunology
Interleukin-12 / biosynthesis
Molecular Structure
Peptides / chemical synthesis*
Peptides / chemistry
Peptides / immunology*
Vaccines / immunology*

Substances

Epitopes
Histocompatibility Antigens Class I
Peptides
Vaccines
Interleukin-12
8-hydroxyadenine
Adenine