Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Publication DOI: 10.1039/9781849739993-00209Publisher: Royal Society of Chemistry
Editors: Jesús Jiménez-Barbero J, Canada FJ, Martín-Santamaría S
Correspondence: stephane.vincent
unamur.be
Institutions: University of Namur, Département de Chimie, Laboratoire de Chimie Bio-Organique, Namur, Belgium
Galactofuranose, the atypical and thermodynamically disfavored form of D-galactose, has in reality a very old history in chemistry and biochemistry. Indeed, synthetic methods to produce galactofuranosides selectively date back to the beginning of the 20th century. Moreover, in 1937, Haworth et al. found that the extracellular polysaccharide ‘‘galactocarolose’’ produced by Penicillium charlesii contains galactose in a furanose configuration. The search for biosynthetic precursors rapidly began and, in 1970, it was found that when galactocarolose biosynthesis was inhibited, UDP-galactofuranose (UDP-Galf) accumulated. UDP-Galf was thus identified as a likely biosynthetic precursor of galactofuranosides. One year later, while studying the T1 antigen of Salmonella typhimurium, Nikaido and Sarvas speculated that UDP-galactopyranose (UDP-Galp) was the precursor of UDP-Galf. However, the first gene that, unambiguously, could be attributed to the conversion of UDP-Galp into its furanose form was only identified and cloned in 1996 and the first galactofuranosyltransferase was discovered at the very beginning of the 21st century. As we will detail below, the Galf-processing enzymes happen to proceed through unique or rarely occurring mechanisms. Meanwhile, galactofuranose moieties have also been identified in the cell wall of major pathogens. Therefore, interest into the biosynthesis of galactofuranose and the search for glycomimetics of galactofuranose have grown rapidly in recent years. The purpose of this chapter is to give an overview of the fundamental aspects of the galactofuranose biosynthesis, from the biological occurrence to the search for inhibitors. Several review articles partially covering some aspects of this topic have been published in the literature and will be cited in each paragraph.
biosynthesis, bacteria, galactofuranose, fungi, reaction mechanics
Structure type: oligomer
Location inside paper: p. 212, paragraph 1, Fig. 9.2B
Trivial name: galactan-I O-antigen
Compound class: galatan
Contained glycoepitopes: IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,SB_7
Comments, role: review; one of the moieties that constitute O-antigen
Related record ID(s): 42335, 48522, 48523, 48524, 48529
NCBI Taxonomy refs (TaxIDs): 83333,
573,
1010799Reference(s) to other database(s): GTC:G93691ZU
Show glycosyltransferases
There is only one chemically distinct structure:
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