First total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6'-amino-6'-deoxy-alpha-D-glucosyl)-sn-glycerol--a glycoglycerolipid of a marine alga with a high inhibitor activity against human Myt1-kinase.
The first total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6'-amino-6'-deoxy-alpha-D-glucosyl)-sn-glycerol, a glycoglycerolipid isolated from a marine alga extract, is described. Starting from alpha-methylglucopyranoside the multistep strategy allows the stereoselective synthesis of the final compound using various protective group procedures as well as derivatization of partial molecule domains. The latter offers the development of lead structures for inhibitors of human Myt1-kinase.
Göllner
Christiane
C
Department of Medicinal Chemistry, Martin-Luther-University Halle-Wittenberg, W.-Langenbeck-Str.4, 06120 Halle, Germany.
Philipp
Claudia
C
Dobner
Bodo
B
Sippl
Wolfgang
W
Schmidt
Matthias
M
D056890:Eukaryota / Q000737:chemistry*; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007700:Kinetics; D008565:Membrane Proteins; D015394:Molecular Structure; D009792:Oceans and Seas; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017346:Protein Serine-Threonine Kinases / Q000037:antagonists & inhibitors*; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors*
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