Taxonomic group: bacteria / Actinobacteria
(Phylum: Actinobacteria)
Associated disease: Crohn disease [ICD11:
DD70 
]
NCBI PubMed ID: 36867005Publication DOI: 10.1021/acs.orglett.3c00378Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: S.S. Kulkarni <suvarn
chem.iitb.ac.in>
Institutions: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, Maharashtra 400076, India
A short and efficient methodology has been developed to synthesize an analogue of a lipooligosaccharide from Mycobacterium linda isolated from Crohn's disease. The total synthesis of the tetrasaccharide was achieved via a convergent [2 + 2] glycosylation approach. The key features of the synthesis involve the selective functionalization of a trehalose core via highly regioselective acylations and regioselective glycosylations. The synthesis was completed via a longest linear sequence of 14 steps in a 14.2% overall yield.
Lipooligosaccharide, glycosylation, total synthesis, Crohn's disease, Mycobacterium linda
Structure type: oligomer
Location inside paper: p. 1717, Fig. 1, compound 1
Compound class: LOS
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158539,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, FTIR, UV, glycosylation, optical rotation measurement, CC, HR-ESI-MS
NCBI Taxonomy refs (TaxIDs): 1763
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error