(1S,2R/1R,2S)-ainocyclohexyl glycyl thymine PNA: synthesis, monomer crystal structures, and DNA/RNA hybridization studies.
[structure: see text] The synthesis of ethyl cis-(1S,2R/1R,2S)-2-aminocyclohex-1-yl-N-(thymin-1-yl-acetyl) glycinate (10a and 10b) via enzymatic resolution of the key racemic intermediate trans-2-azido cyclohexanols 3 is reported. The crystal structures of 10 show equatorial disposition of the tertiary amide group, with the torsion angle beta in the range 60-70 degrees. The PNA oligomers incorporating these show differential effects in hybridizing with complementary DNA and RNA.
Govindaraju
T
T
Division of Organic Chemistry (Synthesis) and Centre for Materials Characterisation (X-ray Facility), National Chemical Laboratory, Pune 411008, India.
Gonnade
Rajesh G
RG
Bhadbhade
Mohan M
MM
Kumar
Vaijayanti A
VA
Ganesh
Krishna N
KN
D016956:Burkholderia cepacia / Q000201:enzymology; D002175:Candida / Q000201:enzymology; D018360:Crystallography, X-Ray; D018076:DNA, Complementary / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009693:Nucleic Acid Hybridization / Q000379:methods; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018075:RNA, Complementary / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013941:Thymine / Q000031:analogs & derivatives*
D018076:DNA, Complementary; D020135:Peptide Nucleic Acids; D018075:RNA, Complementary; D008049:Lipase; D013941:Thymine