Complete 1 H NMR assignment of cholesteryl benzoate

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

© 2018 Elsevier Inc. The 750 MHz 1 H NMR spectrum of cholesteryl benzoate (1b) could be assigned completely, which means all chemical shifts and all coupling constants, including some long-range values, were established. This task was possible by extracting many approximate coupling constant values in the overlapped spectrum region from an HSQC experiment, and using these values in the 1 H iterative full spin analysis integrated in the PERCH NMR software. The task was facilitated using our published data for 3β-acetoxypregna-5,16-dien-20-one (3), the assignment data of the sesquiterpene benzoquinone dihydroperezone (2), also performed in the present study, which contains the same carbon atoms chain than cholesterol (1a), and an HSQC study of (25R)-27-deuteriocholesterol (1c) we prepared some 40 years ago. The HSQC values of 1c in combination with the coupling constants of 1b also allowed to completely assigning the spectrum of 1c. The complete assignment of 1b and 1c further provided the opportunity to estimate the hydrogen shifts induced upon benzoylation of cholesterol. Comparison of the experimental vicinal coupling constants of 1b with the values calculated using the Altona software provides an excellent correlation. In addition, a single crystal X-ray diffraction study of 1b provided the molecular conformation in the solid state, which revealed the side chain adopts an extended conformation.
Original languageAmerican English
Pages (from-to)72-81
Number of pages63
JournalSteroids
DOIs
StatePublished - 1 Oct 2018

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Conformations
Software
Cholesterol
Nuclear magnetic resonance
Molecular Conformation
Sesquiterpenes
Chemical shift
X-Ray Diffraction
Hydrogen
Carbon
Single crystals
X ray diffraction
Atoms
Experiments
cholesteryl benzoate
2-benzoquinone

Cite this

@article{7f012b2d777242a2a2d7a25b1ad64260,
title = "Complete 1 H NMR assignment of cholesteryl benzoate",
abstract = "{\circledC} 2018 Elsevier Inc. The 750 MHz 1 H NMR spectrum of cholesteryl benzoate (1b) could be assigned completely, which means all chemical shifts and all coupling constants, including some long-range values, were established. This task was possible by extracting many approximate coupling constant values in the overlapped spectrum region from an HSQC experiment, and using these values in the 1 H iterative full spin analysis integrated in the PERCH NMR software. The task was facilitated using our published data for 3β-acetoxypregna-5,16-dien-20-one (3), the assignment data of the sesquiterpene benzoquinone dihydroperezone (2), also performed in the present study, which contains the same carbon atoms chain than cholesterol (1a), and an HSQC study of (25R)-27-deuteriocholesterol (1c) we prepared some 40 years ago. The HSQC values of 1c in combination with the coupling constants of 1b also allowed to completely assigning the spectrum of 1c. The complete assignment of 1b and 1c further provided the opportunity to estimate the hydrogen shifts induced upon benzoylation of cholesterol. Comparison of the experimental vicinal coupling constants of 1b with the values calculated using the Altona software provides an excellent correlation. In addition, a single crystal X-ray diffraction study of 1b provided the molecular conformation in the solid state, which revealed the side chain adopts an extended conformation.",
author = "Nury P{\'e}rez-Hern{\'a}ndez and Elvia Becerra-Mart{\'i}nez and Pedro Joseph-Nathan",
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language = "American English",
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Complete 1 H NMR assignment of cholesteryl benzoate. / Pérez-Hernández, Nury; Becerra-Martínez, Elvia; Joseph-Nathan, Pedro.

In: Steroids, 01.10.2018, p. 72-81.

Research output: Contribution to journalArticle

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AB - © 2018 Elsevier Inc. The 750 MHz 1 H NMR spectrum of cholesteryl benzoate (1b) could be assigned completely, which means all chemical shifts and all coupling constants, including some long-range values, were established. This task was possible by extracting many approximate coupling constant values in the overlapped spectrum region from an HSQC experiment, and using these values in the 1 H iterative full spin analysis integrated in the PERCH NMR software. The task was facilitated using our published data for 3β-acetoxypregna-5,16-dien-20-one (3), the assignment data of the sesquiterpene benzoquinone dihydroperezone (2), also performed in the present study, which contains the same carbon atoms chain than cholesterol (1a), and an HSQC study of (25R)-27-deuteriocholesterol (1c) we prepared some 40 years ago. The HSQC values of 1c in combination with the coupling constants of 1b also allowed to completely assigning the spectrum of 1c. The complete assignment of 1b and 1c further provided the opportunity to estimate the hydrogen shifts induced upon benzoylation of cholesterol. Comparison of the experimental vicinal coupling constants of 1b with the values calculated using the Altona software provides an excellent correlation. In addition, a single crystal X-ray diffraction study of 1b provided the molecular conformation in the solid state, which revealed the side chain adopts an extended conformation.

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