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

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.