title: Synthesis of glycoglycerolipid of 1,2-dipalmitoyl-3-(N-palmitoyl-6'-amino-6'-deoxy-α-D-glucosyl)-sn-glycerol and its analogues, inhibitors of human Myt1-kinase.
abstract: A glycoglycerolipid 1a isolated from a marine alga showed inhibition to Myt1 kinase with IC(50) of 0.12 μg/mL. We synthesized 1a and its seven analogues (1b-h) in an efficient method with high stereoselectivity. The process employed trichloroacetimidate donor 4b at low substrate concentration to achieve high α-selectivity (α/β=33:1) in glycosylation reaction. The present synthesis provided various acyl derivatives required for the study on the structure-activity relationship later.
authors.affiliation: Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China.
authors.forename: Yihua
authors.initials: Y
authors.lastname: Sun
authors.forename: Jun
authors.initials: J
authors.lastname: Zhang
authors.forename: Chunxia
authors.initials: C
authors.lastname: Li
authors.forename: Huashi
authors.initials: H
authors.lastname: Guan
authors.forename: Guangli
authors.initials: G
authors.lastname: Yu
mesh_terms: D004305:Dose-Response Relationship, Drug; D006017:Glycolipids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D006801:Humans; D008565:Membrane Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D015394:Molecular Structure; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017346:Protein Serine-Threonine Kinases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C545327:1,2-dipalmitoyl-3-(N-palmitoyl-6-amino-6-deoxyglucosyl)-sn-glycerol; D006017:Glycolipids; D008565:Membrane Proteins; D047428:Protein Kinase Inhibitors; C015903:glycerolglycolipids; D011505:Protein-Tyrosine Kinases; C490679:PKMYT1 protein, human; D017346:Protein Serine-Threonine Kinases