Synthesis of a tetrasaccharide phosphate from the linkage region of the arabinogalactan-peptidoglycan complex in the mycobacterial cell wall.
The synthesis of dibenzyl 6-O-naphthylmethyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1-->5)-2,3-di-O-benzoyl-6-O-benzyl-beta-D-galactofuranosyl-(1-->4)-3-O-benzyl-2-O-pivaloyl-alpha-l-rhamnopyranosyl-(1-->3)-2-acetamido-2-deoxy-4,6-di-O-benzoyl-alpha-D-glucopyranosyl phosphate (1), a protected form of the tetrasaccharide phosphate of the linkage region of the arabinogalactan-peptidoglycan complex in the mycobacterial cell wall, has been accomplished. Key steps include the coupling of four monosaccharide building blocks with complete stereoselectivity by glycosylations employing thioglycosides, 2'-carboxybenzyl glycosides, and glycosyl fluorides as glycosyl donors. The alpha-glycosyl phosphate linkage was also stereoselectively elaborated by reaction of a tetrasaccharide hemiacetal with tetrabenzyl pyrophosphate in the presence of a base.
Center for Bioactive Molecular Hybrids and Department of Chemistry Yonsei University, Seodaemun-Gu, Seoul, Republic of Korea.
Yong Joo
YJ
Lee
Dinanath Baburao
DB
Fulse
Kwan Soo
KS
Kim
D005685:Galactans / Q000138:chemical synthesis*; D009169:Mycobacterium tuberculosis / Q000737:chemistry*; D009171:Mycolic Acids / Q000138:chemical synthesis*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010457:Peptidoglycan / Q000737:chemistry*; D011134:Polysaccharides / Q000138:chemical synthesis*; D013403:Sugar Phosphates / Q000138:chemical synthesis*
D005685:Galactans; D009171:Mycolic Acids; D009844:Oligosaccharides; D010457:Peptidoglycan; D011134:Polysaccharides; D013403:Sugar Phosphates; C030080:araban