Neurotrophic peptide aldehydes: solid phase synthesis of fellutamide B and a simplified analog.
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.
Schneekloth
John S
JS
Department of Molecular, Cellular, and Developmental Biology, Yale University, PO Box 208103, New Haven, CT 06520-8103, USA.
Sanders
John L
JL
Hines
John
J
Crews
Craig M
CM
D000447:Aldehydes / Q000138:chemical synthesis* / Q000494:pharmacology; D000595:Amino Acid Sequence; D000818:Animals; D002460:Cell Line; D003500:Cyclization; D004151:Dipeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D005347:Fibroblasts / Q000473:pathology; D006801:Humans; D020128:Inhibitory Concentration 50; D055666:Lipopeptides; D051379:Mice; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009375:Neoplasms, Glandular and Epithelial / Q000473:pathology; D009414:Nerve Growth Factors / Q000378:metabolism; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010673:Pheochromocytoma / Q000473:pathology; D051381:Rats; D013431:Sulfates / Q000737:chemistry
D000447:Aldehydes; D004151:Dipeptides; D055666:Lipopeptides; D009414:Nerve Growth Factors; D009842:Oligopeptides; D013431:Sulfates; C513652:fellutamide B; C080556:fellutamide A