title: Preparation of various lysogangliosides including lyso-fucosyl GM1 and delayed extraction matrix-assisted laser desorption ionization time-of-flight mass spectrometric analysis.
abstract: Our rapid method of microwave-mediated saponification for preparing lysoglycosphingolipids from their parent glycosphingolipids was also able to prepare lysogangliosides or modified lysogangliosides, which were identified by delayed extraction matrix-assisted laser desorption ionization time-of-flight mass spectrometric (DE MALDI-TOF MS) analysis. When GM3, GM2, and GM1 isolated from adult human brain gangliosides were subjected to the saponification, GM3 was found to give rise to only lyso-GM3 containing de-N-acetylneuraminic acid (de-N-acetyl lyso-GM3), whereas the GM2 produced both lyso-GM2 and the de-N-acetyl compound, and GM1 also gave both lyso-GM1 and the de-N-acetyl compound. In the saponification of GM1 and GDla, isolated from rat brain gangliosides, GM1 similarly produced both lyso-GM1 and the de-N-acetyl compound, but GDla was found to give rise to both dehydrated de-N-monoacetyl and dehydrated de-N-diacetyl lyso-GDla. However, the saponification of the GM1 fraction isolated from porcine brain gangliosides gave rise not only to both lyso-GM1 and the de-N-acetyl compound, but also unexpectedly to both lyso-fucosyl GM1 and its de-N-acetyl compound. The untreated GM1 fraction was examined by TLC and DE MALDI-TOF mass spectrometry, and proved to contain fucosyl-GM1. The DE MALDI-TOF MS analysis of the prepared lyso-gangliosides showed that their long chain bases consisted of d18:1 and d20:1 sphingosines in various ratios reflecting those of the different mammalian brain gangliosides.
authors.affiliation: Department of Biochemistry, Shinshu University, School of Medicine, Nagano. agingol@gipac.shinshu-u.ac.jp
authors.forename: T
authors.initials: T
authors.lastname: Taketomi
authors.forename: A
authors.initials: A
authors.lastname: Hara
authors.forename: K
authors.initials: K
authors.lastname: Uemura
authors.forename: H
authors.initials: H
authors.lastname: Kurahashi
authors.forename: E
authors.initials: E
authors.lastname: Sugiyama
mesh_terms: D000328:Adult; D000818:Animals; D001923:Brain Chemistry; D002240:Carbohydrate Sequence; D005677:G(M1) Ganglioside / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005678:G(M2) Ganglioside / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005679:G(M3) Ganglioside / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D005732:Gangliosides / Q000737:chemistry; D006736:Horses; D006801:Humans; D008872:Microwaves; D008969:Molecular Sequence Data; D008970:Molecular Weight; D051381:Rats; D012794:Sialic Acids / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization / Q000379:methods*; D013552:Swine
chemical_list: D005679:G(M3) Ganglioside; D005732:Gangliosides; D012794:Sialic Acids; C056605:lyso-G(M3) ganglioside; C106506:lyso-fucosyl GM1; C029465:lysoGM1 ganglioside; C048941:lysoganglioside G(M2); C021298:ganglioside, GD1a; D005678:G(M2) Ganglioside; D005677:G(M1) Ganglioside; C039123:fucosyl GM1 ganglioside