Novel phosphorus-containing glycosphingolipids from the blowfly Calliphora 
vicina Meigen. Structural analysis by 1H and 1H[31P]-edited NMR spectroscopy at 
600 and 500 megahertz

Dabrowski, Ursula; Dabrowski, Janusz; Helling, Friedhelm; Wiegandt, Herbert

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Novel phosphorus-containing glycosphingolipids from the blowfly Calliphora vicina Meigen. Structural analysis by 1H and 1H[31P]-edited NMR spectroscopy at 600 and 500 megahertz

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Dabrowski, Ursula
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Dabrowski, Janusz
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Dabrowski, U., Dabrowski, J., Helling, F., & Wiegandt, H. (1990). Novel phosphorus-containing glycosphingolipids from the blowfly Calliphora vicina Meigen. Structural analysis by 1H and 1H[31P]-edited NMR spectroscopy at 600 and 500 megahertz. The Journal of Biological Chemistry, 265(17), 9737-9743. Retrieved from http://www.jbc.org/content/265/17/9737.abstract.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-ACF6-6

Abstract

Two novel phosphorus-containing neutral glycosphingolipids of the arthro series were isolated from the blowfly Calliphora vicina Meigen: GalNAc alpha 1----4GalNAc beta 1----(X---- 6)4GlcNAc beta 1----3Man beta 1----4Glc beta 1----1-ceramide and GalNAc beta 1----(X----6)4GlcNAc beta 1----3Man beta 1----4Glc beta 1----1- ceramide (X = -O-P(O)(O-)-OC-H2CH2NH3+). The primary structure of the ceramide pentasaccharide was elucidated de novo using two-dimensional 1H NMR correlation spectroscopy at 500 MHz and multistep relayed coherence transfer spectroscopy at 600 MHz. Localization of the 2'-aminoethyl phosphate substituent was established with the aid of 1H-detected, 31P-edited NMR spectroscopy at 500/202 MHz.