Synthesis of carba-NAD and the structures of its ternary complexes with SIRT3 and SIRT5

J Org Chem. 2012 Sep 7;77(17):7319-29. doi: 10.1021/jo301067e. Epub 2012 Aug 17.

Abstract

Carba-NAD is a synthetic compound identical to NAD except for one substitution, where an oxygen atom adjacent to the anomeric linkage bearing nicotinamide is replaced with a methylene group. Because it is inert in nicotinamide displacement reactions, carba-NAD is an unreactive substrate analogue for NAD-consuming enzymes. SIRT3 and SIRT5 are NAD-consuming enzymes that are potential therapeutic targets for the treatment of metabolic diseases and cancers. We report an improved carba-NAD synthesis, including a pyrophosphate coupling method that proceeds in approximately 60% yield. We also disclose the X-ray crystal structures of the ternary complexes of SIRT3 and SIRT5 bound to a peptide substrate and carba-NAD. These X-ray crystal structures provide critical snapshots of the mechanism by which human sirtuins function as protein deacylation catalysts.

MeSH terms

  • Carbasugars / chemical synthesis*
  • Carbasugars / chemistry*
  • Carbasugars / metabolism
  • Crystallography, X-Ray
  • Humans
  • Models, Molecular
  • Molecular Structure
  • NAD / chemical synthesis*
  • NAD / chemistry*
  • NAD / metabolism
  • Sirtuin 3 / chemistry*
  • Sirtuin 3 / metabolism
  • Sirtuins / chemistry*
  • Sirtuins / metabolism
  • Stereoisomerism

Substances

  • Carbasugars
  • NAD
  • SIRT5 protein, human
  • Sirtuin 3
  • Sirtuins