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.
Copyright © 2013 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Carbohydrate Conformation
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Galactolipids / chemical synthesis*
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Galactolipids / chemistry
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Galactolipids / pharmacology
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Humans
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Membrane Proteins / antagonists & inhibitors
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Membrane Proteins / metabolism
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Protein Kinase Inhibitors / chemical synthesis*
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Protein Kinase Inhibitors / chemistry
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Protein Kinase Inhibitors / pharmacology
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Protein Serine-Threonine Kinases / antagonists & inhibitors
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Protein Serine-Threonine Kinases / metabolism
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Protein-Tyrosine Kinases / antagonists & inhibitors
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Protein-Tyrosine Kinases / metabolism
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Structure-Activity Relationship
Substances
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6'-acylamido-6'-deoxy-alpha-D-galactoglycerolipid
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Galactolipids
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Membrane Proteins
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Protein Kinase Inhibitors
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Protein-Tyrosine Kinases
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PKMYT1 protein, human
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Protein Serine-Threonine Kinases