Document Detail

Sequence dependent N-terminal rearrangement and degradation of peptide nucleic acid (PNA) in aqueous solution.
MedLine Citation:
PMID:  11543609     Owner:  NASA     Status:  MEDLINE    
The stability of the PNA (peptide nucleic acid) thymine monomer ¿N-[2-(thymin-1-ylacetyl)]-N-(2-aminoaminoethyl)glycine¿ and those of various PNA oligomers (5-8-mers) have been measured at room temperature (20 degrees C) as a function of pH. The thymine monomer undergoes N-acyl transfer rearrangement with a half-life of 34 days at pH 11 as analyzed by 1H NMR; and two reactions, the N-acyl transfer and a sequential degradation, are found by HPLC analysis to occur at measurable rates for the oligomers at pH 9 or above. Dependent on the amino-terminal sequence, half-lives of 350 h to 163 days were found at pH 9. At pH 12 the half-lives ranged from 1.5 h to 21 days. The results are discussed in terms of PNA as a gene therapeutic drug as well as a possible prebiotic genetic material.
M Eriksson; L Christensen; J Schmidt; G Haaima; L Orgel; P E Nielsen
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Nouveau journal de chimie     Volume:  22     ISSN:  0398-9836     ISO Abbreviation:  Nouv J Chim     Publication Date:  1998  
Date Detail:
Created Date:  1999-10-22     Completed Date:  1999-10-22     Revised Date:  2001-09-04    
Medline Journal Info:
Nlm Unique ID:  7801282     Medline TA:  Nouv J Chim     Country:  FRANCE    
Other Details:
Languages:  eng     Pagination:  1055-9     Citation Subset:  S    
Dept. of Biochemistry B, The Panum Institute, Copenhagen, Denmark.
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MeSH Terms
Evolution, Chemical*
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Peptide Nucleic Acids / chemical synthesis,  chemistry*
Polymers / chemical synthesis,  chemistry*
Thymine / analogs & derivatives*
Water / chemistry*
Reg. No./Substance:
0/Peptide Nucleic Acids; 0/Polymers; 0/Solutions; 65-71-4/Thymine; 7732-18-5/Water
L E Orgel / U CA San Diego, La Jolla

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