Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 4, Pages 1509-1516Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo802211n
Keywords
-
Categories
Funding
- National Institutes of Health [GM076251-01, EY08098, 5P50 CA097190-04]
- Applied Biosystems
- Mellon College of Sciences
Ask authors/readers for more resources
A general method for preparing optically pure guanidine-based gamma-peptide nucleic acid (gamma GPNA) monomers for all four natural nucleobases (A, C, G, and T) is described. These second-generation gamma GPNAs 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 (x-predecessors, which are randomly folded, gamma GPNAs 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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available