One-flask syntheses of c-di-GMP and the [Rp,Rp] and [Rp,Sp] thiophosphate analogues.
An integrated set of reactions and conditions that allow an eight-step one-flask synthesis of the protected derivatives of c-di-GMP and the [R(p),R(p)] and [R(p),S(p)] thiophosphate analogues is reported. Deprotection is also carried out as a one-flask procedure, with the final products isolated by crystallization from the reaction mixture. Chromatography is only used for separation of the thiophosphate diastereomers.
Gaffney
Barbara L
BL
Department of Chemistry and Chemical Biology, 610 Taylor Road, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
Veliath
Elizabeth
E
Zhao
Jianwei
J
Jones
Roger A
RA
D006152:Cyclic GMP / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007700:Kinetics; D010710:Phosphates / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D010710:Phosphates; C062025:bis(3',5')-cyclic diguanylic acid; D006152:Cyclic GMP; C035638:thiophosphoric acid