Document Detail

Synthesis of a C-linked glycosylated thymine-based PNA monomer and its incorporation into a PNA oligomer.
MedLine Citation:
PMID:  16990940     Owner:  NLM     Status:  MEDLINE    
Backbone modification of peptide nucleic acids (PNAs) by glycosylation has been shown to enhance selective biodistribution and cellular targeting of PNA oligomers based on sugar and cell surface lectin interactions. Here we report the synthesis of a new backbone-glycosylated thymine-based PNA monomer (T(gal)). The sugar residue was attached to the backbone of PNA via a stable carbon-carbon linkage between the sugar and the PNA monomers. Also, incorporation of the modified monomer into a PNA decamer (H-Ala(gal)-G-G-G-T(gal)-C-A-G-C-T(gal)-T-Lys-NH2) was successfully performed. Melting temperature (UV-Tm) of the modified PNA against the complementary DNA was only slightly lower than unmodified PNA.
Ramin Hamzavi; Christoph Meyer; Nils Metzler-Nolte
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2006-08-17
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  4     ISSN:  1477-0520     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2006 Oct 
Date Detail:
Created Date:  2006-09-22     Completed Date:  2007-08-28     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  3648-51     Citation Subset:  IM    
Institute for Pharmacy and Molecular Biotechnology, University of Heidelberg, Im Neuenheimer Feld 364, 69120, Heidelberg, Germany.
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MeSH Terms
Carbon / chemistry*
Peptide Nucleic Acids / chemical synthesis*,  chemistry*
Thymine / chemistry*
Reg. No./Substance:
0/Peptide Nucleic Acids; 65-71-4/Thymine; 7440-44-0/Carbon

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