title: A simplified procedure for gram-scale production of sialylglycopeptide (SGP) from egg yolks and subsequent semi-synthesis of Man3GlcNAc oxazoline.
abstract: Heterogeneity of glycan structures in native glycoconjugates always hampers precise studies on carbohydrate-involved biological functions. To construct homogeneous glycoconjugates from natural resource of homogeneous glycans is therefore a practical approach to solve this problem. We report here an optimized procedure for gram-scale production of sialylglycopeptide (SGP) containing a disialyl biantennary complex-type N-glycan from egg yolks. Our new procedure simplified the extraction process by treating the egg yolk powder with 40% acetone, avoiding massive emulsification, high-speed centrifugation, and sophisticated chromatography in reported methods. Subsequent semi-synthesis of the N-glycan core Man3GlcNAc oxazoline from SGP was accomplished for the first-time via glyco-trimming and successive oxazoline formation. This efficient semi-synthesis provides an alternative to the pure chemical approach that involves multi-step total synthesis and facilitates the application of endo-glycosidase-enabled chemoenzymatic synthesis of various homogeneous glycoconjugates.
authors.affiliation: Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China; CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, China.
authors.forename: Bingyang
authors.initials: B
authors.lastname: Sun
authors.affiliation: CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, China; iHuman Institute, ShanghaiTech University, Shanghai 201210, China.
authors.forename: Wenzheng
authors.initials: W
authors.lastname: Bao
authors.affiliation: CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, China.
authors.forename: Xiaobo
authors.initials: X
authors.lastname: Tian
authors.affiliation: CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, China; iHuman Institute, ShanghaiTech University, Shanghai 201210, China.
authors.forename: Mingjing
authors.initials: M
authors.lastname: Li
authors.affiliation: CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, China.
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
authors.affiliation: Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China. Electronic address: dongjh66@hotmail.com.
authors.forename: Jinhua
authors.initials: J
authors.lastname: Dong
authors.affiliation: CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Pudong, Shanghai 201203, China; iHuman Institute, ShanghaiTech University, Shanghai 201210, China. Electronic address: huangwei@simm.ac.cn.
authors.forename: Wei
authors.initials: W
authors.lastname: Huang
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry; D055162:Biocatalysis; D002851:Chromatography, High Pressure Liquid; D003890:Desiccation; D004527:Egg Proteins / Q000737:chemistry / Q000302:isolation & purification*; D004530:Egg Yolk / Q000737:chemistry; D006031:Glycosylation; D017038:Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010080:Oxazoles / Q000138:chemical synthesis*; D012795:Sialoglycoproteins / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D001426:Bacterial Proteins; D004527:Egg Proteins; D009844:Oligosaccharides; D010080:Oxazoles; D012795:Sialoglycoproteins; D017038:Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase
keywords: Chemoenzymatic transglycosylation; Egg yolk; Man3GlcNAc oxazoline; Sialylglycopeptide