Synthesis and properties of chiral peptide nucleic acids with a N-aminoethyl-D-proline backbone.
A synthon of D-proline substituted at the 4-position by thymine and at N by a flexible aminoethyl linker, has been used to prepare a novel chiral peptide nucleic acid (cPNA) with (2R,4R) stereochemistry using solid phase methodology. The homothymine decamer cPNA binds to complementary polyadenylic acid to form a 2:1 hybrid with high affinity and specificity according to UV and CD studies, whereas no binding to the corresponding polydeoxyadenylic acid was observed.
Vilaivan
T
T
Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Patumwan, Bangkok, Thailand.
Khongdeesameor
C
C
Harnyuttanakorn
P
P
Westwell
M S
MS
Lowe
G
G
D002942:Circular Dichroism; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
C420964:N-(aminoethyl)proline; D020135:Peptide Nucleic Acids; D011392:Proline