Premium
Plaxyloside from the Marine Sponge Plakortis simplex : an Improved Strategy for NMR Structural Studies of Carbohydrate Chains
Author(s) -
Costantino Valeria,
Fattorusso Ernesto,
Imperatore Concetta,
Mangoni Alfonso
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200112)2001:23<4457::aid-ejoc4457>3.0.co;2-g
Subject(s) - chemistry , pyranose , aglycone , carbohydrate , stereochemistry , nuclear magnetic resonance spectroscopy , computational chemistry , organic chemistry , glycoside
Plaxyloside, a glycolipid composed of a C 35 linear polyisoprenoid alcohol aglycone and a linear carbohydrate chain made up of six β‐xylopyranose units, has been isolated as its peracetate from the Caribbean sponge Plakortis simplex , and its structure determined on the basis of spectral and chemical data. Study of plaxyloside showed that: (a) carbohydrate chains with repetitive structures can be conveniently studied as their peracetates by NMR spectroscopy in C 6 D 6 , thanks to the peculiar conformational behavior of these derivatives, and (b) coupling constant analysis can be used to establish relative configurations in pyranose sugars even in the presence of conformational equilibria.