2017
DOI: 10.1021/acs.joc.7b02485
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Semisynthesis of Complex-Type Biantennary Oligosaccharides Containing Lactosamine Repeating Units from a Biantennary Oligosaccharide Isolated from a Natural Source

Abstract: Poly-N-acetyllactosamine (poly-LacNAc) structures on glycoproteins play important roles in essential biological events such as cell-cell adhesion. Here, we report a new strategy for the semisynthesis of LacNAc-extended complex-type biantennary oligosaccharides. We found an efficient isopropylidenation reaction that selectively protects the terminal Gal-3,4-OH of a biantennary complex-type nonasaccharide isolated from a natural source. This finding enabled the conversion of the nonasaccharide into the two types… Show more

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Cited by 10 publications
(10 citation statements)
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“…Unfortunately, these methods provide precursors that have several terminal GlcNAc or Gal moieties and therefore cannot be elaborated in a branch selective manner to yield compounds having unique appendages at each antenna. Ingenuous protecting group manipulations have been employed to convert a naturally derived oligosaccharide into glycosyl acceptors that can then be diversified by chemical glycosylation 23,47 . However, this approach involves several low yielding steps and has limited capability to prepare compounds with complex branching patterns.…”
Section: Resultsmentioning
confidence: 99%
“…Unfortunately, these methods provide precursors that have several terminal GlcNAc or Gal moieties and therefore cannot be elaborated in a branch selective manner to yield compounds having unique appendages at each antenna. Ingenuous protecting group manipulations have been employed to convert a naturally derived oligosaccharide into glycosyl acceptors that can then be diversified by chemical glycosylation 23,47 . However, this approach involves several low yielding steps and has limited capability to prepare compounds with complex branching patterns.…”
Section: Resultsmentioning
confidence: 99%
“…Based on the established semisynthesis, we can easily access complicated molecules in 10 steps and perform biological studies using the homogeneous substrates. This strategy also enabled us to synthesize a N acetyllactosamine repeated biantennary oligosaccharide 15 and would be useful to prepare various complex type oligosaccharides and glycoproteins.…”
Section: Synthesis Of Triantennary Oligosaccharidesmentioning
confidence: 99%
“…Sialylglycopeptide (SGP) was also found in hen's egg yolk and digested by PNGase, one of the most highly specific glycosidases extensively used in enzymatic isolation (Seko et al, 1997). Chemical modification of SGP to various other glycoproteins has been developed by Kajihara's group, which achieved semi-synthesis of poly-LacNAc containing complex-type biantennary oligosaccharide (Maki et al, 2017) and was recently applied to triantennary erythropoietin (EPO) N-glycan (Maki et al, 2020).…”
Section: Introductionmentioning
confidence: 99%