Synthesis of alpha-P-modified nucleoside diphosphates with ethylenediamine.
This report describes a one-pot synthesis of alpha-P-borano-, alpha-P-thio-, and alpha-P-seleno-modified nucleoside diphosphate analogues that are otherwise difficult to obtain. The key step involves the intramolecular nucleophilic attack by an amino group in 5 to remove the gamma-phosphate. The absolute configurations of P-diastereomers were confirmed by analysis of their 1H NMR. Affinity studies revealed that the nucleoside boranodiphosphates are potentially useful in antiviral research.
Li
Ping
P
Department of Chemistry, Duke University, Durham, North Carolina 27708-0346, USA.
Xu
Zhihong
Z
Liu
Hongyan
H
Wennefors
Charlotta K
CK
Dobrikov
Mikhail I
MI
Ludwig
János
J
Shaw
Barbara Ramsay
BR
D000244:Adenosine Diphosphate / Q000031:analogs & derivatives; D000818:Animals; D003402:Creatine Kinase / Q000378:metabolism; D005029:Ethylenediamines / Q000737:chemistry*; D008968:Molecular Conformation; D009132:Muscles / Q000201:enzymology / Q000378:metabolism; D009711:Nucleotides / Q000138:chemical synthesis* / Q000378:metabolism; D011770:Pyruvate Kinase / Q000378:metabolism; D011817:Rabbits
D005029:Ethylenediamines; D009711:Nucleotides; C031234:ethylenediamine; D000244:Adenosine Diphosphate; D011770:Pyruvate Kinase; D003402:Creatine Kinase