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.
Highlights
Two novel phosphorus-containing neutral glycosphingolipids of the arthro series were isolated from the blowfly Calliphora vicina Meigen: GalNAccul+
Thanks to the variety of NMR methods available at present, many different strategies for de nova structure elucidation are possible [3,4,5], and a choice often depends on practical aspects, e.g. on the possibility of recording a string of experiments with unchanged hardware configuration of the spectrometer during a weekend. This motive induced us to choose an assignment strategy based on conventional two-dimensional correlation spectroscopy (COSY) [6] and two, three, and four-step relayed coherence transfer (RCT-1, -2, and -3)
Further component separation was achieved by straight-phase high pressure liquid chromatography (HPLC) on a column made of 40 ml of Silica Gel 60
Summary
Two novel phosphorus-containing neutral glycosphingolipids of the arthro series were isolated from the blowfly Calliphora vicina Meigen: GalNAccul+. With the hope of finding comparable biological situations that would permit a possible extrapolation to function, we undertook the investigation of GSL occurring in species that are, to vertebrates, highly evolved, but members of a different phylogenetic tree, such as the Diptera among insects Investigations to this end were initiated by elucidating the structures of eight neutral GSL of the blowfly Calliphora uicina Meigen [1, 2]. Thanks to the variety of NMR methods available at present, many different strategies for de nova structure elucidation are possible [3,4,5], and a choice often depends on practical aspects, e.g. on the possibility of recording a string of experiments with unchanged hardware configuration of the spectrometer during a weekend This motive induced us to choose an assignment strategy based on conventional two-dimensional correlation spectroscopy (COSY) [6] and two-, three-, and four-step relayed coherence transfer (RCT-1, -2, and -3). Overhauser enhancement (NOE) spectrum in the rotating frame (ROESY) (8-ll), and localization of the P’-aminoethyl phosphate substituent was established by means of heteronuclear phosphorus-edited proton NMR spectroscopy [12]
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