A two-step strategy for the preparation of 6-deoxy-l-sorbose

Wen, Liuqing; Huang, Kenneth; Zheng, Yu; Liu, Yunpeng; Zhu, He; Wang, Peng George

doi:10.1016/j.bmcl.2016.03.083

Cited by 5 publications

(2 citation statements)

References 32 publications

(30 reference statements)

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“…Inorganic pyrophosphatase PPA was added to the reaction mixture to hydrolyze the newly formed inorganic pyrophosphate to improve the overall yields. Products 4 , 8 , 9 , 12 , and 13 were purified by a silver nitrate precipitation method. , Silver nitrate precipitation is a newly developed method used for the purification of phosphorylated sugars, by which sugar adenosines (ATP and ADP) can be cleanly precipitated out of aqueous solution while sugar phosphates (with five or more than five carbons) are still in solution. , This method has widely been used for sugar phosphate purification. − We noticed that silver nitrate could also cleanly precipitate other phosphorylated nucleotides such as UTP and UDP in aqueous solution, while sugar nucleotides with one or two internal phosphate groups (UDP-sugars, GDP-sugars, and CMP-sugars) were not affected. Therefore, once the aforementioned reactions were finished, excess silver nitrate was added to precipitate ATP, ADP, and UTP.…”

Section: Resultsmentioning

confidence: 99%

Chemoenzymatic Synthesis of Unnatural Nucleotide Sugars for Enzymatic Bioorthogonal Labeling

et al. 2018

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In recent years, the development of the enzymatic bioorthogonal labeling strategy has offered exciting possibilities in the probing of structure-defined glycan epitopes. This strategy takes advantage of relaxed donor specificity and strict acceptor specificity of glycosyltransferases to label target glycan epitopes with bioorthogonal reactive groups carried by unnatural nucleotide sugars in vitro. The subsequent covalent conjugation by bioorthogonal chemical reactions with either fluorescent or affinity tags allows further visualization, quantification, or enrichment of target glycan epitopes. However, the application and development of the enzymatic labeling strategy have been hindered due to the limited availability of unnatural nucleotide sugars. Herein, a platform that combines chemical synthesis and enzymatic synthesis for the facile preparation of unnatural nucleotide sugars modified with diverse bioorthogonal reactive groups is described. By this platform, a total of 25 UDP-GlcNAc and UDP-GalNAc derivatives, including the most well explored bioorthogonal functional groups, were successfully synthesized. Furthermore, the potential application of these compounds for use in enzymatic bioorthogonal labeling reactions was also evaluated.

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Section: Resultsmentioning

confidence: 99%

Chemoenzymatic Synthesis of Unnatural Nucleotide Sugars for Enzymatic Bioorthogonal Labeling

et al. 2018

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“… This yield can be increased to 94% by the inclusion of sugar nucleotide regeneration systems . In addition, enzyme-catalyzed reactions can be carried out in one pot (one-pot multienzyme strategy) because of the substrate specificity of enzymes. ,− …”

Section: Overview Of Oligosaccharide Synthesismentioning

confidence: 99%

Toward Automated Enzymatic Synthesis of Oligosaccharides

et al. 2018

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Oligosaccharides together with oligonucleotides and oligopeptides comprise the three major classes of natural biopolymers. Automated systems for oligonucleotide and oligopeptide synthesis have significantly advanced developments in biological science by allowing nonspecialists to rapidly and easily access these biopolymers. Researchers have endeavored for decades to develop a comparable general automated system to synthesize oligosaccharides. Such a system would have a revolutionary impact on the understanding of the roles of glycans in biological systems. The main challenge to achieving automated synthesis is the lack of general synthetic methods for routine synthesis of glycans. Currently, the two main methods to access homogeneous glycans and glycoconjugates are chemical synthesis and enzymatic synthesis. Enzymatic glycosylation can proceed stereo- and regiospecifically without protecting group manipulations. Moreover, the reaction conditions of enzyme-catalyzed glycosylations are extremely mild when compared to chemical glycosylations. Over the past few years methodology toward the automated chemical synthesis of oligosaccharides has been developed. Conversely, while automated enzymatic synthesis is conceptually possible, it is not as well developed. The goal of this survey is to provide a foundation on which continued technological advancements can be made to promote the automated enzymatic synthesis of oligosaccharides.

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