Synthesis of homoceramides, novel ceramide analogues, and their lack of effect on the growth of hippocampal neurons

S De Jonghe, I Lamote, K Venkataraman…

Index: De Jonghe, Steven; Lamote, Inge; Venkataraman, Krishnan; Boldin, Swetlana A.; Hillaert, Ulrik; Rozenski, Jef; Hendrix, Chris; Busson, Roger; De Keukeleire, Denis; Van Calenbergh, Serge; Futerman, Anthony H.; Herdewijn, Piet Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 988 - 996

Full Text: HTML

Citation Number: 16

Abstract

The synthesis of a new series of d-erythro-homoceramide analogues is described. Several synthetic approaches were investigated. Homoceramides can be successfully synthesized from l-homoserine as chiral building block and a protected Weinreb-amide as a key intermediate. The synthesis of short-chain analogues with a heptyl side chain, as well as with a phenyl residue in the sphingoid part (instead of the naturally occurring tridecyl side ...

Related Articles:

Synthesis and evaluation of acyl protein thioesterase 1 (APT1) inhibitors

[Biel, Markus; Deck, Patrick; Giannis, Athanassios; Waldmann, Herbert Chemistry - A European Journal, 2006 , vol. 12, # 15 p. 4121 - 4143]

Synthesis of a trisubstituted 1, 4-diazepin-3-one-based dipeptidomimetic as a novel molecular scaffold

[Weitz, Iris S.; Pellegrini, Maria; Mierke, Dale F.; Chorev, Michael Journal of Organic Chemistry, 1997 , vol. 62, # 8 p. 2527 - 2534]

Synthesis of eight stereoisomers of pochonicine: nanomolar inhibition of β-N-acetylhexosaminidases

[Hernandez, J. Nicolas; Crisostomo, Fernando R. Pinacho; Martin, Tomas; Martin, Victor S. European Journal of Organic Chemistry, 2007 , # 30 p. 5050 - 5058]

A convenient synthesis of l-α-vinylglycine from l-homoserine lactone

[Berkowitz, David B.; Smith, Marianne K. Synthesis, 1996 , # 1 p. 39 - 41]

Use of L-aspartic acid β-semialdehyde in the synthesis of more complex non protein amino acids

[Baldwin, J. E.; Flinn, A. Tetrahedron Letters, 1987 , vol. 28, # 31 p. 3605 - 3608]

More Articles...