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Hansen E, Limé E, Norrby PO, et al. Anomeric Effects in Sulfamides. J Phys Chem A. 2016;120(20):3677-82doi: 10.1021/acs.jpca.6b02757.
Hansen, E., Limé, E., Norrby, P. O., & Wiest, O. (2016). Anomeric Effects in Sulfamides. The journal of physical chemistry. A, 120(20), 3677-82. https://doi.org/10.1021/acs.jpca.6b02757
Hansen, Eric, et al. "Anomeric Effects in Sulfamides." The journal of physical chemistry. A vol. 120,20 (2016): 3677-82. doi: https://doi.org/10.1021/acs.jpca.6b02757
Hansen E, Limé E, Norrby PO, Wiest O. Anomeric Effects in Sulfamides. J Phys Chem A. 2016 May 26;120(20):3677-82. doi: 10.1021/acs.jpca.6b02757. Epub 2016 May 10. PMID: 27135551; PMCID: PMC5542809.
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J Phys Chem A. 2016 May 26;120(20):3677-82. doi: 10.1021/acs.jpca.6b02757. Epub 2016 May 10.

Anomeric Effects in Sulfamides.

The journal of physical chemistry. A

Eric Hansen, Elaine Limé, Per-Ola Norrby, Olaf Wiest

Affiliations

  1. Department of Chemistry and Biochemistry, University of Notre Dame , Notre Dame, Indiana 46556, United States.
  2. Pharmaceutical Technology and Development, AstraZeneca , Pepparedsleden 1, SE-431 83 Mölndal, Sweden.
  3. Lab of Computational Chemistry and Drug Design, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen 518055, China.

PMID: 27135551 PMCID: PMC5542809 DOI: 10.1021/acs.jpca.6b02757

Abstract

Sulfamides, together with their simpler sulfonamide analogs, are common functional groups in a significant number of biologically active compounds. This is partly due to their unique electronic structure and conformational behavior, which mimics the tetrahedral intermediate involved in many proteases, esterases, and related enzymes. Here, the origin of these unique structural elements are analyzed in the context of a coupled, double anomeric effect using DFT calculations, including conformational scans, and NBO analysis. It is shown that these coupled interactions can be implicitly parametrized in MM3* type force fields using the quantum-guided molecular mechanics (Q2MM) method, yielding accurate force field parameters for molecular mechanics studies of sulfamides and sulfonamides.

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