How recent knowledge on furano-specific enzymes has renewed interest for the synthesis of glycofuranosyl-containing conjugates - Carbohydrate Chemistry: Chemical and Biological Approaches - page 401

How recent knowledge on furano-specific
enzymes has renewed interest for the
synthesis of glycofuranosyl-containing
conjugates
Vincent Ferri ` res,* a,b Caroline Nugier-Chauvin, a,b
Laurent Legentil a,b and Sylvain Tranchimand a,b
DOI: 10.1039/9781849739986-00401
D -Galactose in its furanose form is undoubtedly an enigma in glycosciences that has
triggered numerous chemical, physical and biological studies over the last thirty years. This
chapter is dedicated to show how chemists have been inspired by enzymes involved in the
biosynthesis and metabolism of furanosyl-containing conjugates. The resulting molecular
tools have proven to be essential for better understanding mutases, furanosyl transferases
and furanosyl hydrolases, their impact, their activity and the corresponding biochemical
pathways. Moreover, this chapter includes some examples highlighting the use of modern
NMR techniques and of molecular biology as new tools in chemical laboratories that
contributed to the elucidation of mechanism pathways and/or to the production of new
biocatalysts useful for the synthesis of furanosyl-containing conjugates.
1 Introduction
Sweden Academy of Sciences awarded E. Fischer in 1902 for his predic-
tion of parentage of carbohydrates, the stereochemical elucidation of
these highly stereogenic simple blocks, and, very importantly too, for
their striking ability to adopt several forms, so that sugars can be drawn
either linearly or as a five- (furanose) or a six-membered (pyranose) ring.
To this major discovery in the field of natural molecules followed many
efforts in analytical approaches, chemical modifications and synthesis.
However, because mammals are able to biosynthesize only pyranosyl-
containing conjugates and polymers, with the exception of nucleic
acids, the scientific community was mainly attracted by biomolecules
bearing sugars in a pyranose form. Recently, an increased attention has
been turned towards hexofuranosides as such scaffolds were clearly
established to be present in glycans from bacteria, mycobacteria,
archaebacteria, or fungi. 1,2 They are also found in plants and in some
marine sponges and starfish. 1,2 Moreover, some furanosidic structures
were identified at the surface of proteins, thus demonstrating that
carbohydrates in this five-membered ring geometry can be involved
in post-translational maturation of proteins. 3 The main furanosidic
structures were found to be L -arabinose ( L -Ara) in plants and bacteria,