One-flask syntheses of c-di-GMP and the [Rp,Rp] and [Rp,Sp] thiophosphate analogues

Org Lett. 2010 Jul 16;12(14):3269-71. doi: 10.1021/ol101236b.

Abstract

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Cyclic GMP / analogs & derivatives*
  • Cyclic GMP / chemical synthesis
  • Cyclic GMP / chemistry
  • Kinetics
  • Phosphates / chemical synthesis*
  • Phosphates / chemistry*
  • Stereoisomerism

Substances

  • Phosphates
  • bis(3',5')-cyclic diguanylic acid
  • Cyclic GMP
  • thiophosphoric acid