Identification and substructure analysis of oligosaccharide chains derived from glycoproteins by computer retrieval of high‐resolution ¹H‐NMR spectra

Abstract

SUMMARYBased on a statistical model of the reproducibility of NMR spectral features, a system for computer retrieval of high-resolution 'H-NMR spectra of glycoprotein carbohydrates has been developed. For corresponding peaks in an unknown and a reference spectrum, a similarity index based on the reproducibility of the chemical shifts is calculated. In addition, a second similarity index, based on the probability distribution of the percentage of non-matching peaks, has been developed. From these two similarity indices, a combined similarity index using the recall-reliability function as the optimizing criterion has been derived.First results indicate that the "H-NMR reproducibility-based retrieval' ('1HRR') system offers good perspectives for both identification and substructure analysis.

Carbohydrate Structural Determination by NMR Spectroscopy: Modern Methods and Limitations

“…Several groups have worked on developing different concepts based on both 1 H NMR data 57,58,[63][64][65]85,[187][188][189][190] and 13 C NMR data. [60][61][62][63][64][65]85,187 A short description of the methodology behind some of the programs is given below.…”

“…Vliegenthart and co-workers developed a 1 H and 13 C NMR database, SUGABASE, which combines CarbBank and Complex Carbohydrate Structure Data (CCSD) with proton and carbon 92 chemical shifts in a search routine. 57,58,189,191 The search is based on the use of 1 H chemical shifts from the structural reporter groups. 56 This concept is based on the fact that it is often sufficient to inspect only certain areas of a spectrum to ascertain the primary structure of a common glycoprotein carbohydrate structure.…”