Preparation of a naturally occurring D-erythro-(2S,3R)- sphingosylphosphocholine using Shewanella alga NS-589

Noriyuki Sueyoshi, Hiroyuki Izu, Makoto Ito

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Sphingosylphosphocholine, an N-deacylated derivative of sphingomyelin, has been found to be involved in many cellular events. This paper describes a new method for preparation of a D-erythro-sphingosylphosphocholine, which is naturally occurring but difficult to prepare by chemical methods, using marine bacteria as a biocatalyst. When cultured with Shewanella alga NS-589 in synthetic medium, sphingomyelin was found to be efficiently converted by sphingomyelin deacylase to sphingosylphosphocholine. Sphingosylphosphocholine was purified with a high yield from the culture supernatant and identified to be a D-erythro-(2S,3R)-isomer containing d18:1 sphingenine as a long-chain base by fast atom bombardment mass spectrometry and NMR analyses.

Original languageEnglish
Pages (from-to)1923-1927
Number of pages5
JournalJournal of Lipid Research
Volume38
Issue number9
Publication statusPublished - Sep 1 1997

Fingerprint

Shewanella
Algae
Sphingomyelins
Fast Atom Bombardment Mass Spectrometry
Isomers
Mass spectrometry
Bacteria
Nuclear magnetic resonance
Derivatives
Atoms
sphingosine phosphorylcholine
Enzymes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Endocrinology
  • Cell Biology

Cite this

Preparation of a naturally occurring D-erythro-(2S,3R)- sphingosylphosphocholine using Shewanella alga NS-589. / Sueyoshi, Noriyuki; Izu, Hiroyuki; Ito, Makoto.

In: Journal of Lipid Research, Vol. 38, No. 9, 01.09.1997, p. 1923-1927.

Research output: Contribution to journalArticle

Sueyoshi, Noriyuki ; Izu, Hiroyuki ; Ito, Makoto. / Preparation of a naturally occurring D-erythro-(2S,3R)- sphingosylphosphocholine using Shewanella alga NS-589. In: Journal of Lipid Research. 1997 ; Vol. 38, No. 9. pp. 1923-1927.
@article{f7a982ce486743d3b0de35ad88370abe,
title = "Preparation of a naturally occurring D-erythro-(2S,3R)- sphingosylphosphocholine using Shewanella alga NS-589",
abstract = "Sphingosylphosphocholine, an N-deacylated derivative of sphingomyelin, has been found to be involved in many cellular events. This paper describes a new method for preparation of a D-erythro-sphingosylphosphocholine, which is naturally occurring but difficult to prepare by chemical methods, using marine bacteria as a biocatalyst. When cultured with Shewanella alga NS-589 in synthetic medium, sphingomyelin was found to be efficiently converted by sphingomyelin deacylase to sphingosylphosphocholine. Sphingosylphosphocholine was purified with a high yield from the culture supernatant and identified to be a D-erythro-(2S,3R)-isomer containing d18:1 sphingenine as a long-chain base by fast atom bombardment mass spectrometry and NMR analyses.",
author = "Noriyuki Sueyoshi and Hiroyuki Izu and Makoto Ito",
year = "1997",
month = "9",
day = "1",
language = "English",
volume = "38",
pages = "1923--1927",
journal = "Journal of Lipid Research",
issn = "0022-2275",
publisher = "American Society for Biochemistry and Molecular Biology Inc.",
number = "9",

}

TY - JOUR

T1 - Preparation of a naturally occurring D-erythro-(2S,3R)- sphingosylphosphocholine using Shewanella alga NS-589

AU - Sueyoshi, Noriyuki

AU - Izu, Hiroyuki

AU - Ito, Makoto

PY - 1997/9/1

Y1 - 1997/9/1

N2 - Sphingosylphosphocholine, an N-deacylated derivative of sphingomyelin, has been found to be involved in many cellular events. This paper describes a new method for preparation of a D-erythro-sphingosylphosphocholine, which is naturally occurring but difficult to prepare by chemical methods, using marine bacteria as a biocatalyst. When cultured with Shewanella alga NS-589 in synthetic medium, sphingomyelin was found to be efficiently converted by sphingomyelin deacylase to sphingosylphosphocholine. Sphingosylphosphocholine was purified with a high yield from the culture supernatant and identified to be a D-erythro-(2S,3R)-isomer containing d18:1 sphingenine as a long-chain base by fast atom bombardment mass spectrometry and NMR analyses.

AB - Sphingosylphosphocholine, an N-deacylated derivative of sphingomyelin, has been found to be involved in many cellular events. This paper describes a new method for preparation of a D-erythro-sphingosylphosphocholine, which is naturally occurring but difficult to prepare by chemical methods, using marine bacteria as a biocatalyst. When cultured with Shewanella alga NS-589 in synthetic medium, sphingomyelin was found to be efficiently converted by sphingomyelin deacylase to sphingosylphosphocholine. Sphingosylphosphocholine was purified with a high yield from the culture supernatant and identified to be a D-erythro-(2S,3R)-isomer containing d18:1 sphingenine as a long-chain base by fast atom bombardment mass spectrometry and NMR analyses.

UR - http://www.scopus.com/inward/record.url?scp=0030863335&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030863335&partnerID=8YFLogxK

M3 - Article

VL - 38

SP - 1923

EP - 1927

JO - Journal of Lipid Research

JF - Journal of Lipid Research

SN - 0022-2275

IS - 9

ER -