Applications of Vibrational Optical Activity in the Pharmaceutical Industry

Nafie, L. A.; Dukor, Rina K.

doi:10.1002/9780470027325.s8906

Cited by 41 publications

(68 citation statements)

References 74 publications

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“…Vibrational optical activity (VOA) [1][2][3][4][5] occurs in two principal forms, infrared vibrational circular dichroism, known as VCD, and vibrational Raman optical activity, known as ROA. In recent years, particular attention has been devoted to the methodology of the determination of absolute configuration (AC) in chiral molecules using VCD [6][7][8][9][10].…”

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confidence: 99%

Vibrational Circular Dichroism: A New Tool for the Solution-State Determination of the Structure and Absolute Configuration of Chiral Natural Product Molecules

Nafie

2008

Natural Product Communications

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This paper is dedicated to Professor Pedro Joseph-Nathan for his 65 th birthday. Vibrational circular dichroism (VCD) has been used in recent years to determine the absolute configuration of a number of natural product chiral molecules. In this brief review, these applications will be described and the methodology of VCD determination of absolute configuration (AC) will be explained. The principal advantages of VCD versus X-ray crystallography for absolute configuration determination are: 1) only solution-state samples are needed and therefore single crystals are not required, 2) high enantiomeric sample purity is not required, 3) high chemical purity is not required as long as impurities are not chiral and 4) solution-state conformations are obtained as an extra feature of the AC determination.

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confidence: 99%

Vibrational Circular Dichroism: A New Tool for the Solution-State Determination of the Structure and Absolute Configuration of Chiral Natural Product Molecules

Nafie

2008

Natural Product Communications

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“…Frequencies and rotational strengths are given in Table S1. (5) 0.97 0.99 0.99 0.89 (5) 0.95 4 866 0.96 0.79 0.86 0.92 (5) 0.91 (5) 0.89 (5) 0.94 0.92 5 890 0.90 0.99 0.92 (3) 0.96 (4) 0.95 (4) 0.96 (4) 0.90 (3) 1.00 1.00 1.00 1.00 0.96 1.00 (13) 1.00 0.99 13 2246 1.00 0.99 1.00 1.00 0.96 1.00 (12) 1.00 0.99 14 3050 1.00 1.00 1.00 (15) 1.00 0.94 1.00 1.00 0.99 15 3056 1.00 1.00 1.00 (14) 1.00 0.94 1.00 1.00 0.99 a Nomenclature of DFTB parametrizations is abbreviated. b Integers between parentheses next to the overlaps indicate with which nth BP86/TZP mode occurs the largest overlap.…”

Section: The Journal Of Physical Chemistry Amentioning

confidence: 99%

Use of Density Functional Based Tight Binding Methods in Vibrational Circular Dichroism

et al. 2018

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Vibrational circular dichroism (VCD) is a spectroscopic technique used to resolve the absolute configuration of chiral systems. Obtaining a theoretical VCD spectrum requires computing atomic polar and axial tensors on top of the computationally demanding construction of the force constant matrix. In this study we evaluated a VCD model in which all necessary quantities are obtained with density functional based tight binding (DFTB) theory. The analyzed DFTB parametrizations fail at providing accurate vibrational frequencies and electric dipole gradients but yield reasonable normal modes at a fraction of the computational cost of density functional theory (DFT). Thus, by applying DFTB in composite methods along with DFT, we show that it is possible to obtain accurate VCD spectra at a much lower computational demand.

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“…A table summarizing the chiral drugs whose ACs were investigated [34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63,64,65,66,67,68,69,70,71,72,73,74,75,76,77,78,79,80,81,82,83,84,85,86,87,88,89,90] using chiroptical spectroscopic methods are summarized in Table 1. Occasional reviews have also highlighted some of these chiral drugs [42,65,91,92]. There are several natural products with promising medicinal values where ACs were investigated using chiroptical spectroscopy, but it will be unwieldy to review all of them here.…”

Section: Chiroptical Spectroscopic Toolsmentioning

confidence: 99%

Determination of the Absolute Configurations of Chiral Drugs Using Chiroptical Spectroscopy

Polavarapu

2016

Molecules

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Chiroptical spectroscopy has emerged as a promising tool for the determination of absolute configurations and predominant conformations of chiral molecules in academic laboratories. This promise has led to the adaption of chiroptical spectroscopic methods as valuable tools in chiral drug discovery research programs of the pharmaceutical industry. Most major pharmaceutical companies have invested in in-house chiroptical spectroscopy applications and reported successful outcomes. In the context of continuously increasing applications of chiroptical spectroscopy for chiral molecular structure determination, a review of recent developments and applications for chiral drugs is presented in this manuscript.

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Applications of Vibrational Optical Activity in the Pharmaceutical Industry

Cited by 41 publications

References 74 publications

Vibrational Circular Dichroism: A New Tool for the Solution-State Determination of the Structure and Absolute Configuration of Chiral Natural Product Molecules

Vibrational Circular Dichroism: A New Tool for the Solution-State Determination of the Structure and Absolute Configuration of Chiral Natural Product Molecules

Use of Density Functional Based Tight Binding Methods in Vibrational Circular Dichroism

Determination of the Absolute Configurations of Chiral Drugs Using Chiroptical Spectroscopy

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