Document Detail

Synthesis of conformationally preorganized and cell-permeable guanidine-based gamma-peptide nucleic acids (gammaGPNAs).
MedLine Citation:
PMID:  19161276     Owner:  NLM     Status:  MEDLINE    
A general method for preparing optically pure guanidine-based gamma-peptide nucleic acid (gammaGPNA) monomers for all four natural nucleobases (A, C, G, and T) is described. These second-generation gammaGPNAs differ from the first-generation GPNAs in that the guanidinium group is installed at the gamma- instead of the alpha-position of the N-(2-aminoethyl)glycine backbone unit. This positional switch enables GPNAs to be synthesized from relatively cheap L- as opposed to D-amino acids. Unlike their alpha-predecessors, which are randomly folded, gammaGPNAs prepared from L-amino acids are preorganized into a right-handed helix and bind to DNA and RNA with exceptionally high affinity and sequence selectivity and are readily taken up by mammalian cells.
Bichismita Sahu; Venugopal Chenna; Kira L Lathrop; Sufi M Thomas; Gerald Zon; Kenneth J Livak; Danith H Ly
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  74     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2009 Feb 
Date Detail:
Created Date:  2009-02-16     Completed Date:  2009-04-28     Revised Date:  2014-09-17    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1509-16     Citation Subset:  IM    
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MeSH Terms
Base Sequence
Cell Membrane Permeability*
DNA / metabolism
Guanidine / chemistry*
HeLa Cells
Liver / cytology
Nucleic Acid Conformation*
Nucleic Acid Hybridization
Peptide Nucleic Acids / chemical synthesis,  chemistry*,  metabolism*
RNA / metabolism
Substrate Specificity
Grant Support
5P50 CA097190-04/CA/NCI NIH HHS; EY08098/EY/NEI NIH HHS; GM076251-01/GM/NIGMS NIH HHS; R01 GM077261/GM/NIGMS NIH HHS; R01 GM077261-03/GM/NIGMS NIH HHS
Reg. No./Substance:
0/Peptide Nucleic Acids; 63231-63-0/RNA; 9007-49-2/DNA; JU58VJ6Y3B/Guanidine

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