Biochemistry of the sphingolipids: XII. conversion of cerebrosides to ceramides and sphingosine; structure of Gaucher cerebroside*

An improved procedure for the conversion of cerebroside to ceramide and sphingosine has been devised, consisting of periodate opening of the glycosidic ring, reduction with NaBH4, and hydrolysis under very mild acid conditions to ceramide. The over-all yield is excellent and only the erythro isomer...

Full description

Bibliographic Details
Main Authors: H.E. Carter, J.A. Rothfus, Roy Gigg
Format: Article
Language:English
Published: Elsevier 1961-07-01
Series:Journal of Lipid Research
Online Access:http://www.sciencedirect.com/science/article/pii/S002222752039009X
_version_ 1818925329278828544
author H.E. Carter
J.A. Rothfus
Roy Gigg
author_facet H.E. Carter
J.A. Rothfus
Roy Gigg
author_sort H.E. Carter
collection DOAJ
description An improved procedure for the conversion of cerebroside to ceramide and sphingosine has been devised, consisting of periodate opening of the glycosidic ring, reduction with NaBH4, and hydrolysis under very mild acid conditions to ceramide. The over-all yield is excellent and only the erythro isomer results. Alkaline hydrolysis of ceramide gives erythro-sphingosine in good yield. Application of this procedure to Gaucher cerebroside has shown it to contain the “normal” erythro-sphingosine.
first_indexed 2024-12-20T02:39:29Z
format Article
id doaj.art-79c2045714e14b328a41f498b40c02e8
institution Directory Open Access Journal
issn 0022-2275
language English
last_indexed 2024-12-20T02:39:29Z
publishDate 1961-07-01
publisher Elsevier
record_format Article
series Journal of Lipid Research
spelling doaj.art-79c2045714e14b328a41f498b40c02e82022-12-21T19:56:21ZengElsevierJournal of Lipid Research0022-22751961-07-0123228234Biochemistry of the sphingolipids: XII. conversion of cerebrosides to ceramides and sphingosine; structure of Gaucher cerebroside*H.E. Carter0J.A. Rothfus1Roy Gigg2Division of Biochemistry, Noyes Laboratory of Chemistry, University of Illinois, Urbana, IllinoisDivision of Biochemistry, Noyes Laboratory of Chemistry, University of Illinois, Urbana, IllinoisDivision of Biochemistry, Noyes Laboratory of Chemistry, University of Illinois, Urbana, IllinoisAn improved procedure for the conversion of cerebroside to ceramide and sphingosine has been devised, consisting of periodate opening of the glycosidic ring, reduction with NaBH4, and hydrolysis under very mild acid conditions to ceramide. The over-all yield is excellent and only the erythro isomer results. Alkaline hydrolysis of ceramide gives erythro-sphingosine in good yield. Application of this procedure to Gaucher cerebroside has shown it to contain the “normal” erythro-sphingosine.http://www.sciencedirect.com/science/article/pii/S002222752039009X
spellingShingle H.E. Carter
J.A. Rothfus
Roy Gigg
Biochemistry of the sphingolipids: XII. conversion of cerebrosides to ceramides and sphingosine; structure of Gaucher cerebroside*
Journal of Lipid Research
title Biochemistry of the sphingolipids: XII. conversion of cerebrosides to ceramides and sphingosine; structure of Gaucher cerebroside*
title_full Biochemistry of the sphingolipids: XII. conversion of cerebrosides to ceramides and sphingosine; structure of Gaucher cerebroside*
title_fullStr Biochemistry of the sphingolipids: XII. conversion of cerebrosides to ceramides and sphingosine; structure of Gaucher cerebroside*
title_full_unstemmed Biochemistry of the sphingolipids: XII. conversion of cerebrosides to ceramides and sphingosine; structure of Gaucher cerebroside*
title_short Biochemistry of the sphingolipids: XII. conversion of cerebrosides to ceramides and sphingosine; structure of Gaucher cerebroside*
title_sort biochemistry of the sphingolipids xii conversion of cerebrosides to ceramides and sphingosine structure of gaucher cerebroside
url http://www.sciencedirect.com/science/article/pii/S002222752039009X
work_keys_str_mv AT hecarter biochemistryofthesphingolipidsxiiconversionofcerebrosidestoceramidesandsphingosinestructureofgauchercerebroside
AT jarothfus biochemistryofthesphingolipidsxiiconversionofcerebrosidestoceramidesandsphingosinestructureofgauchercerebroside
AT roygigg biochemistryofthesphingolipidsxiiconversionofcerebrosidestoceramidesandsphingosinestructureofgauchercerebroside