2021
DOI: 10.3390/molecules26092450
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Computational NMR of Carbohydrates: Theoretical Background, Applications, and Perspectives

Abstract: This review is written amid a marked progress in the calculation of NMR parameters of carbohydrates substantiated by a vast amount of experimental data coming from several laboratories worldwide. By no means are we trying to cover in the present compilation a huge amount of all available data. The main idea of the present review was only to outline general trends and perspectives in this dynamically developing area on the background of a marked progress in theoretical and computational NMR. Presented material … Show more

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Cited by 28 publications
(29 citation statements)
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References 163 publications
(352 reference statements)
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“…A collection of single-residue 13 C-labeled hexasaccharides permitted to break the chemical shift degeneracy of the hexamer and experimentally assess some geometrical features of its conformation at the single residue level ( Delbianco et al, 2018 ). Still, a detailed description of the overall shape remained elusive, as “traditional” NMR parameters (i.e., NOEs, J-couplings) are limited to short-range distances ( Valverde et al, 2019b ; Krivdin, 2021 ) and cannot disclose the relative orientation of residues further apart in a linear saccharide chain ( Battistel et al, 2014 ).…”
Section: Introductionmentioning
confidence: 99%
“…A collection of single-residue 13 C-labeled hexasaccharides permitted to break the chemical shift degeneracy of the hexamer and experimentally assess some geometrical features of its conformation at the single residue level ( Delbianco et al, 2018 ). Still, a detailed description of the overall shape remained elusive, as “traditional” NMR parameters (i.e., NOEs, J-couplings) are limited to short-range distances ( Valverde et al, 2019b ; Krivdin, 2021 ) and cannot disclose the relative orientation of residues further apart in a linear saccharide chain ( Battistel et al, 2014 ).…”
Section: Introductionmentioning
confidence: 99%
“…F I G U R E 3 CBS-estimated RMS deviations of (a) carbon and (b) proton isotropic shieldings from the empirical values in methane as a function of the method number (given in the abscissa axis): VXSC (1), HCTH (2), HCTH97 (3), HCTH147 (4), THCTH (5), M06L (6), B97D (7), B3LYP (8), B3P86 (9), B3PW91 (10), B1B95 (11), MPW1PW91 (12), MPW1LYP (13), MPW1PBE (14), MPW3PBE (15), B98 (16), B971 (17), B972 (18), PBE1PBE (19), B1LYP (20), O3LYP (21), BhandH (22), BHandHLYP (23), BMK (24), M06 (25), M06HF (26), M062X (27), tHCTHhyb (28), HSEh1PBE (29), HSE2PBE (30), PBEh1PBE (31), wB97XD (32), wB97 (33), wB97X (34), TPSSh (35), X3LYP (36), LC-wPBE (37), CAM-B3LYP (38), WP04 (39), RHF (40), MP2 (41), KT1 (42), KT2 (43), KT3 (44), SOPPA (45), SOPPA (CCSD) (46), and CCSD(T) (47). Reproduced from Kupka, et al [88] with the permission of the American Chemical Society Much later, Kupka, et al [88] performed a systematic study of the performance of about four dozens of different DFT functionals together with five pure nonempirical methods, RHF, MP2, SOPPA, SOPPA (CCSD), and CCSD(T), for predicting 1 H and 13 C NMR chemical shifts of six small molecules, NH 3 , CH 4 , C 2 H 2 , C 2 H 4 , C 2 H 6 , and C 6 H 6 , with using Jensen's pcS-n (n = 1-4) basis set.…”
Section: Small Moleculesmentioning
confidence: 99%
“…Those seminal papers are discussed in full in the recent reviews. [ 35–38 ] Herewith, we will only illustrate the progress in this field with several most illustrative recent examples, documenting the application of computational NMR to this field.
…”
Section: Computational 1h and 13c Nmr In Stereochemical Studies Of In...mentioning
confidence: 99%
See 1 more Smart Citation
“…Theoretical calculation of 13 C nuclear magnetic resonance (NMR) chemical shifts provides a powerful tool in structural elucidation of organic molecules, natural products, carbohydrates, and biochemical species. [1][2][3][4][5] Continuing our very recent survey of large natural products with multiple asymmetric centers, [6][7][8][9][10][11] current study is focused on the huge tetrakis monoterpene indole alkaloid, alasmontamine A, which is shown below in Figure 1.…”
Section: Introductionmentioning
confidence: 99%