| Synthesis of conformationally preorganized and cell-permeable guanidine-based gamma-peptide nucleic acids (gammaGPNAs). | |
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MedLine Citation:
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PMID: 19161276 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Bichismita Sahu; Venugopal Chenna; Kira L Lathrop; Sufi M Thomas; Gerald Zon; Kenneth J Livak; Danith H Ly |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 74 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2009 Feb |
Date Detail:
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Created Date: 2009-02-16 Completed Date: 2009-04-28 Revised Date: 2013-06-02 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 1509-16 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Center for Nucleic Acids Science and Technology, Carnegie Mellon University, 4400 Fifth Avenue, Pittsburgh, Pennsylvania 15213, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Animals Base Sequence Cell Membrane Permeability* DNA / metabolism Guanidine / chemistry* HeLa Cells Humans Liver / cytology Nucleic Acid Conformation* Nucleic Acid Hybridization Peptide Nucleic Acids / chemical synthesis, chemistry*, metabolism* RNA / metabolism Stereoisomerism Substrate Specificity |
| Grant Support | |
ID/Acronym/Agency:
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5P50 CA097190-04/CA/NCI NIH HHS; EY08098/EY/NEI NIH HHS; GM076251-01/GM/NIGMS NIH HHS; R01 GM077261-03/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Peptide Nucleic Acids; 113-00-8/Guanidine; 63231-63-0/RNA; 9007-49-2/DNA |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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