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Literature DB >> 24371429

Concise Synthesis of the Unnatural Sphingosine and Psychosine Enantiomer.

Archana R Parameswar¹, Jacqueline A Hawkins², Laurel K Mydock¹, Mark S Sands², Alexei V Demchenko¹.

Abstract

The accumulation of psychosine (galactosyl sphingosine) has been associated with the pathogenesis of Krabbe disease, however, the exact mechanism of its cytotoxicity remains unclear. Herein, we describe the synthesis of the unnatural enantiomer of erythrosphingosine, psychosine, and related derivatives thereof that would allow for the mechanistic elucidation of the toxicity of psychosine.

Entities: CellLine Chemical Disease Gene Species

Keywords: carbohydrates; enantiomers; glycosphingolipids; glycosylation; psychosine; sphingosine

Year: 2010 PMID： 24371429 PMCID： PMC3872080 DOI： 10.1002/ejoc.201000024

Source DB: PubMed Journal: European J Org Chem ISSN： 1099-0690

22 in total

1. PHYSIOLOGICAL ACTIVITY OF PSYCHOSINE.

Authors: T TAKETOMI; K NISHIMURA
Journal: Jpn J Exp Med Date: 1964-10

2. Versatile synthesis and mechanism of activation of S-benzoxazolyl glycosides.

Authors: Medha N Kamat; Nigam P Rath; Alexei V Demchenko
Journal: J Org Chem Date: 2007-08-04 Impact factor: 4.354

3. New evidence that both T-type calcium channels and GABAA channels are responsible for the potent peripheral analgesic effects of 5alpha-reduced neuroactive steroids.

Authors: Sriyani Pathirathna; Barbara C Brimelow; Miljen M Jagodic; Kathiresan Krishnan; Xin Jiang; Charles F Zorumski; Steven Mennerick; Douglas F Covey; Slobodan M Todorovic; Vesna Jevtovic-Todorovic
Journal: Pain Date: 2005-04 Impact factor: 6.961

4. Chemoenzymatic Synthesis of All Four Stereoisomers of Sphingosine from Chlorobenzene: Glycosphingolipid Precursors(1)(a).

Authors: Thomas C. Nugent; Tomas Hudlicky
Journal: J Org Chem Date: 1998-02-06 Impact factor: 4.354

5. Enantiodivergent synthesis of D- and L-erythro-sphingosines through Mannich-type reactions of N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone.

Authors: Pedro Merino; Pablo Jimenez; Tomas Tejero
Journal: J Org Chem Date: 2006-06-09 Impact factor: 4.354

Concise Synthesis of the Unnatural Sphingosine and Psychosine Enantiomer.

1. PHYSIOLOGICAL ACTIVITY OF PSYCHOSINE.

2. Versatile synthesis and mechanism of activation of S-benzoxazolyl glycosides.

3. New evidence that both T-type calcium channels and GABAA channels are responsible for the potent peripheral analgesic effects of 5alpha-reduced neuroactive steroids.

4. Chemoenzymatic Synthesis of All Four Stereoisomers of Sphingosine from Chlorobenzene: Glycosphingolipid Precursors(1)(a).

5. Enantiodivergent synthesis of D- and L-erythro-sphingosines through Mannich-type reactions of N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone.

6. Dysfunction of peroxisomes in twitcher mice brain: a possible mechanism of psychosine-induced disease.

7. Progressive accumulation of toxic metabolite in a genetic leukodystrophy.

8. Psychosine accumulates in membrane microdomains in the brain of krabbe patients, disrupting the raft architecture.

9. The role of AMPK in psychosine mediated effects on oligodendrocytes and astrocytes: implication for Krabbe disease.

10. Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor.

1. Psychosine, the cytotoxic sphingolipid that accumulates in globoid cell leukodystrophy, alters membrane architecture.