Acremolin from Acremonium strictum is N(2),3-etheno-2'-isopropyl-1-methylguanine, not a 1H-azirine. Synthesis and structural revision

Org Lett. 2013 May 17;15(10):2370-3. doi: 10.1021/ol400752s. Epub 2013 May 1.

Abstract

The first synthesis of the heterocyclic marine natural product, acremolin, is reported along with the revision of the structure from a 1H-azirine to a substituted N(2),3-ethenoguanine (5-methyl-7-isopropyl-4,5-dihydroimidazo[2,1-b]purine). Additional properties of acremolin are also described including its (1)H-(15)N-HMBC and fluorescence spectra.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acremonium / chemistry*
  • Acremonium / isolation & purification
  • Biological Products / chemistry*
  • Fluorescent Dyes / chemistry
  • Guanine / analogs & derivatives*
  • Guanine / chemical synthesis
  • Guanine / chemistry
  • Molecular Structure
  • Purines / chemical synthesis*
  • Purines / chemistry

Substances

  • Biological Products
  • Fluorescent Dyes
  • N(2),3-etheno-2'-isopropyl-1-methylguanine
  • N(2),3-ethenoguanine
  • N(2),3-ethenoguanine (5-methyl-7-isopropyl-4,5-dihydroimidazo(2,1-b)purine)
  • Purines
  • Guanine