Mollenynes B-E from the marine sponge Spirastrella mollis. Band-selective heteronuclear single quantum coherence for discrimination of bromo-chloro regioisomerism in natural products

J Am Chem Soc. 2015 Sep 30;137(38):12343-51. doi: 10.1021/jacs.5b07858. Epub 2015 Sep 22.

Abstract

Four new chlorobromohydrins, mollenynes B-E, were isolated from the marine sponge Spirastrella mollis collected from Hogsty Reef, Bahamas. Their structures were elucidated by integrated analysis of NMR, MS, and computational methods. A high-resolution band-selective HSQC experiment was developed to identify (13)C NMR signals in samples at the nanomole-scale that arise from Cl-substituted (13)C by exploiting the (35)Cl/(37)Cl isotope shift.

Publication types

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

MeSH terms

  • Animals
  • Biological Products / chemistry*
  • Biological Products / isolation & purification*
  • Chlorohydrins / chemistry*
  • Chlorohydrins / isolation & purification*
  • Molecular Conformation
  • Porifera / chemistry*
  • Quantum Theory*
  • Stereoisomerism

Substances

  • Biological Products
  • Chlorohydrins