Amino/guanidino-functionalized N-(pyrrolidin-2-ethyl)glycine-based pet-PNA: design, synthesis and binding with DNA/RNA.
The N-(pyrrolidin-2-ethyl) glycine-based PNA (pet-PNA) backbone, with 4-amino or 4-guanidino-functionalized pyrrolidine ring, confers constrained conformational flexibility on aegPNA. The oligomers bind to the target DNA and RNA sequences with increased sequence specificity and antiparallel versus parallel orientation selectivity. The easy post-synthetic guanidination gives very good access to the positively charged PNA oligomers.
Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India.
Sachin S
SS
Gokhale
Vaijayanti A
VA
Kumar
D000588:Amines / Q000737:chemistry*; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D019791:Guanidine / Q000737:chemistry*; D015394:Molecular Structure; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis*; D011759:Pyrrolidines / Q000737:chemistry*; D012313:RNA / Q000737:chemistry*; D044366:Transition Temperature
D000588:Amines; D020135:Peptide Nucleic Acids; D011759:Pyrrolidines; D012313:RNA; D004247:DNA; D019791:Guanidine; D005998:Glycine