title: Synthesis of 6'-acylamido-6'-deoxy-α-D-galactoglycerolipids.
abstract: Aminoglycoglycerolipid 1a isolated from an algal extract showed activity against the enzyme Myt1 kinase with an IC50 value of 0.12 μg/mL. Its analogues, 6'-acylamido-6'-deoxy-α-D-galactoglycerolipids (2a-g) were synthesized in an efficient way with high stereoselectivity. The key step was to employ a 4-OAc protecting group of the galactosyl donor 14 as a remote neighboring participation group to give the glycoside with high α-anomeric selectivity (α:β=32:1) in the glycosylation. The preliminary bioactivity screening showed that compound 2g exhibited good inhibition against Myt1 kinase.
authors.affiliation: Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China. lchunxia@ouc.edu.cn
authors.forename: Chunxia
authors.initials: C
authors.lastname: Li
authors.forename: Yihua
authors.initials: Y
authors.lastname: Sun
authors.forename: Jun
authors.initials: J
authors.lastname: Zhang
authors.forename: Zhimin
authors.initials: Z
authors.lastname: Zhao
authors.forename: Guangli
authors.initials: G
authors.lastname: Yu
authors.forename: Huashi
authors.initials: H
authors.lastname: Guan
mesh_terms: D002236:Carbohydrate Conformation; D038983:Galactolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D008565:Membrane Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism; 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; D013329:Structure-Activity Relationship
chemical_list: C000592592:6'-acylamido-6'-deoxy-alpha-D-galactoglycerolipid; D038983:Galactolipids; D008565:Membrane Proteins; D047428:Protein Kinase Inhibitors; D011505:Protein-Tyrosine Kinases; C490679:PKMYT1 protein, human; D017346:Protein Serine-Threonine Kinases