Carbohydrate structure generalization scheme for database-driven simulation of experimental observables, such as NMR chemical shifts

Roman R. Kapaev, Ksenia S. Egorova, Philip V. Toukach

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

Carbohydrates play an immense role in different aspects of life. NMR spectroscopy is the most powerful tool for investigation of these compounds. Nowadays, progress in computational procedures has opened up novel opportunities giving an impulse to the development of new instruments intended to make the research simpler and more efficient. In this paper, we present a new approach for simulating13C NMR chemical shifts of carbohydrates. The approach is suitable for any atomic observables, which could be stored in a database. The method is based on sequential generalization of the chemical surroundings of the atom under prediction and heuristic averaging of database data. Unlike existing applications, the generalization scheme is tuned for carbohydrates, including those containing phosphates, amino acids, alditols, and other non-carbohydrate constituents. It was implemented in the Glycan-Optimized Dual Empirical Spectrum Simulation (GODESS) software, which is freely available on the Internet. In the field of carbohydrates, our approach was shown to outperform all other existing methods of NMR spectrum prediction (including quantum-mechanical calculations) in accuracy. Only this approach supports NMR spectrum simulation for a number of structural features in polymeric structures.

Original languageEnglish
Pages (from-to)2594-2611
Number of pages18
JournalJournal of Chemical Information and Modeling
Volume54
Issue number9
DOIs
StatePublished - 22 Sep 2014
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2014 American Chemical Society.

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