Chemoenzymatic synthesis of lacto-N-tetrasaccharide and sialyl lacto-N-tetrasaccharides

Yao, Wenlong; Yan, Jun; Chen, Xi; Wang, Fengshan; Cao, Hongzhi

doi:10.1016/j.carres.2014.10.017

Cited by 47 publications

(29 citation statements)

References 25 publications

(25 reference statements)

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“…Crystalline 1,3-β-glucans were prepared from sucrose and glucose using sucrose phosphorylase and laminaribiose phosphorylase from E. gracilis (Ogawa et al 2014). The concomitant actions of galactokinase and 1, 3-β-galactosyl-N-acetylhexosamine phosphorylase were used in the chemoenzymatic syntheses of the derivatives of lacto-N-tetraose (Yao et al 2015) and derivatives of GNB (Li et al 2015). UDP-Glc was prepared using engineered E. coli cells expressing sucrose phosphorylase as the catalysts (Weyler and Heinzle 2015).…”

Section: Preparation Of Glycosides By Phosphorylases (Recent Publicatmentioning

confidence: 99%

Diversity of phosphorylases in glycoside hydrolase families

Kitaoka

2015

Appl Microbiol Biotechnol

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Phosphorylases are useful catalysts for the practical preparation of various sugars. The number of known specificities was 13 in 2002 and is now 30. The drastic increase in available genome sequences has facilitated the discovery of novel activities. Most of these novel phosphorylase activities have been identified through the investigations of glycoside hydrolase families containing known phosphorylases. Here, the diversity of phosphorylases in each family is described in detail.

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Section: Preparation Of Glycosides By Phosphorylases (Recent Publicatmentioning

confidence: 99%

Diversity of phosphorylases in glycoside hydrolase families

Kitaoka

2015

Appl Microbiol Biotechnol

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“…To acquire core structures 1 – 5 at gram scales for further enzymatic diversification, a concise chemical approach was designed using 2,6-diol 7 , a known monosaccharide imidate 14 8 , and a disaccharide imidate 15 9 as the key building blocks (Scheme 3). …”

Section: Chemical Synthesis Of Core Structures 1–5mentioning

confidence: 99%

Chemoenzymatic Assembly of Mammalian O‐Mannose Glycans

et al. 2018

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O-Mannose glycans, a family of highly heterogeneous complex glycans account up to 30% of total O-glycans in brain. Previous synthesis and functional studies only focused on the Core M3 O-mannose glycans of α-dystroglycan which are a causative factor for various muscular diseases. In this study, a highly efficient chemoenzymatic strategy was developed that enabled the first collective synthesis of 63 Core M1 and Core M2 O-mannose glycans. This chemoenzymatic strategy features the gram-scale chemical synthesis of 5 judiciously designed core structures, and the diversity-oriented modification of the core structures with 3 enzyme modules to provide 58 complex O-mannose glycans in a linear sequence that does not exceed 4 steps. Of note, 55 of these O-mannose glycans are synthesized for the first time. Using the printed O-mannose glycan array, the human brain protein CD33, a key factor in the modulation of Alzheimer’s disease was identified as strongly binding to sialylated Core M1 and Core M2.

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“…The synthesis of LNT in milligram-scales has been achieved by chemical as well as enzymatic in vitro approaches [18,[22][23][24]. Recently, we have demonstrated the synthesis of LNT by a Escherichia coli whole-cell biotransformation method that converts lactose by a two-step in vivo glycosylation into LNT using the recombinant ␤1,3-N-acetylglucosaminyltransferase (LgtA) and ␤1,3-galactosyltransferase (WbgO) [25].…”

Section: Introductionmentioning

confidence: 99%