Absolute Configuration Assignment of 3′,4′-di-O-acylkhellactones Using Vibrational Circular Dichroism Exciton Chirality

Abigail I. Buendía-Trujillo; J. Martín Torrres-Valencia; Pedro Joseph-Nathan; Eleuterio Burgueño-Tapia

doi:10.1177/1934578X1501000658

Absolute Configuration Assignment of 3′,4′-di-O-acylkhellactones Using Vibrational Circular Dichroism Exciton Chirality

Abigail I. Buendía-Trujillo, J. Martín Torrres-Valencia, Pedro Joseph-Nathan, Eleuterio Burgueño-Tapia

Escuela Nacional de Ciencias Biológicas (ENCB)

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

The 3′R,4‘R absolute configuration (AC) of the angular-type pyranocoumarins (-)-3′,4′-di-O-acetylkhellactone (2), (-)-4′-O-acetyl-3′-O-angeloylkhellactone (3), (+)-3′-O-acetyl-4-O-isobutyroylkhellactone (4), and (-)-3′-O-angeloyl-4′-O-senecioylkhellactone (5), isolated from the aerial parts of Prionosciadum thapsoides, was assigned by vibrational circular dichroism exciton chirality (VCDEC), and confirmed by comparison of their VCD frequencies with those calculated using DFT at the B3LYP/DGDZVP level. This again reveals that AC assignments based on optical rotation data are not very confident. Evaluation of Flack and Hooft parameters obtained after single-crystal X-ray diffraction analysis of 3, independently confirmed this AC.

Original language	English
Journal	Natural Product Communications
Volume	10
Issue number	6
DOIs	https://doi.org/10.1177/1934578X1501000658
State	Published - 2015

Keywords

Absolute configuration
Khellactone derivatives
Prionosciadium thapsoides
Vibrational circular dichroism exciton chirality
X-Ray diffraction

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10.1177/1934578X1501000658

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@article{410d2013944842cab0071bda89431b1e,

title = "Absolute Configuration Assignment of 3′,4′-di-O-acylkhellactones Using Vibrational Circular Dichroism Exciton Chirality",

abstract = "The 3′R,4{\textquoteleft}R absolute configuration (AC) of the angular-type pyranocoumarins (-)-3′,4′-di-O-acetylkhellactone (2), (-)-4′-O-acetyl-3′-O-angeloylkhellactone (3), (+)-3′-O-acetyl-4-O-isobutyroylkhellactone (4), and (-)-3′-O-angeloyl-4′-O-senecioylkhellactone (5), isolated from the aerial parts of Prionosciadum thapsoides, was assigned by vibrational circular dichroism exciton chirality (VCDEC), and confirmed by comparison of their VCD frequencies with those calculated using DFT at the B3LYP/DGDZVP level. This again reveals that AC assignments based on optical rotation data are not very confident. Evaluation of Flack and Hooft parameters obtained after single-crystal X-ray diffraction analysis of 3, independently confirmed this AC.",

keywords = "Absolute configuration, Khellactone derivatives, Prionosciadium thapsoides, Vibrational circular dichroism exciton chirality, X-Ray diffraction",

author = "Buend{\'i}a-Trujillo, {Abigail I.} and Torrres-Valencia, {J. Mart{\'i}n} and Pedro Joseph-Nathan and Eleuterio Burgue{\~n}o-Tapia",

note = "Publisher Copyright: {\textcopyright} 2015 SAGE Publications Inc.",

year = "2015",

doi = "10.1177/1934578X1501000658",

language = "Ingl{\'e}s",

volume = "10",

journal = "Natural Product Communications",

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T1 - Absolute Configuration Assignment of 3′,4′-di-O-acylkhellactones Using Vibrational Circular Dichroism Exciton Chirality

AU - Buendía-Trujillo, Abigail I.

AU - Torrres-Valencia, J. Martín

AU - Joseph-Nathan, Pedro

AU - Burgueño-Tapia, Eleuterio

PY - 2015

Y1 - 2015

N2 - The 3′R,4‘R absolute configuration (AC) of the angular-type pyranocoumarins (-)-3′,4′-di-O-acetylkhellactone (2), (-)-4′-O-acetyl-3′-O-angeloylkhellactone (3), (+)-3′-O-acetyl-4-O-isobutyroylkhellactone (4), and (-)-3′-O-angeloyl-4′-O-senecioylkhellactone (5), isolated from the aerial parts of Prionosciadum thapsoides, was assigned by vibrational circular dichroism exciton chirality (VCDEC), and confirmed by comparison of their VCD frequencies with those calculated using DFT at the B3LYP/DGDZVP level. This again reveals that AC assignments based on optical rotation data are not very confident. Evaluation of Flack and Hooft parameters obtained after single-crystal X-ray diffraction analysis of 3, independently confirmed this AC.

AB - The 3′R,4‘R absolute configuration (AC) of the angular-type pyranocoumarins (-)-3′,4′-di-O-acetylkhellactone (2), (-)-4′-O-acetyl-3′-O-angeloylkhellactone (3), (+)-3′-O-acetyl-4-O-isobutyroylkhellactone (4), and (-)-3′-O-angeloyl-4′-O-senecioylkhellactone (5), isolated from the aerial parts of Prionosciadum thapsoides, was assigned by vibrational circular dichroism exciton chirality (VCDEC), and confirmed by comparison of their VCD frequencies with those calculated using DFT at the B3LYP/DGDZVP level. This again reveals that AC assignments based on optical rotation data are not very confident. Evaluation of Flack and Hooft parameters obtained after single-crystal X-ray diffraction analysis of 3, independently confirmed this AC.

KW - Absolute configuration

KW - Khellactone derivatives

KW - Prionosciadium thapsoides

KW - Vibrational circular dichroism exciton chirality

KW - X-Ray diffraction

UR - http://www.scopus.com/inward/record.url?scp=84969319566&partnerID=8YFLogxK

U2 - 10.1177/1934578X1501000658

DO - 10.1177/1934578X1501000658

M3 - Artículo

SN - 1934-578X

VL - 10

JO - Natural Product Communications

JF - Natural Product Communications

IS - 6

ER -

Absolute Configuration Assignment of 3′,4′-di-O-acylkhellactones Using Vibrational Circular Dichroism Exciton Chirality

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Keywords

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