Abstract
A combination of solid phase and solution phase synthetic methods have been used to complete the total synthesis of the neurotrophic lipopeptide aldehyde fellutamide B (2). The beta-hydroxy aliphatic tail was prepared by regioselective reductive opening of a cyclic sulfate, and later coupled to a solid phase resin. The synthetic compound was then examined in cytotoxicity and nerve growth factor (NGF) induction assays. A simplified analog of fellutamide B also showed activity.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemical synthesis*
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Aldehydes / pharmacology
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Amino Acid Sequence
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Animals
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Cell Line
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Cyclization
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Dipeptides / chemical synthesis*
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Dipeptides / pharmacology
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Fibroblasts / pathology
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Humans
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Inhibitory Concentration 50
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Lipopeptides
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Mice
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Molecular Sequence Data
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Molecular Structure
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Neoplasms, Glandular and Epithelial / pathology
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Nerve Growth Factors / metabolism
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Oligopeptides / chemical synthesis*
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Oligopeptides / chemistry
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Oligopeptides / pharmacology
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Pheochromocytoma / pathology
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Rats
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Sulfates / chemistry
Substances
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Aldehydes
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Dipeptides
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Lipopeptides
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Nerve Growth Factors
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Oligopeptides
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Sulfates
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fellutamide B
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fellutamide A