Chiroptical Properties of Streptorubin B: The Synergy Between Theory and Experiment

Marta Morais Saraiva de Andrade; Vanessa S. Silva; Ana Maria Ferreira da Costa Lourenço; Ana Maria Félix Trindade Lobo; Henry S. Rzepa

doi:10.1002/chir.22486

Chiroptical Properties of Streptorubin B: The Synergy Between Theory and Experiment

Marta Morais Saraiva de Andrade, Vanessa S. Silva, Ana Maria Ferreira da Costa Lourenço, Ana Maria Félix Trindade Lobo, Henry S. Rzepa

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

1 Citation (Scopus)

Abstract

Analysis of the calculated and measured optical rotation (OR) together with other calculated chiroptical properties such as electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of the prodigiosin alkaloid streptorubin B shows that these are dominated by the pseudoenantiomeric atropisomers anti-(S)-streptorubin B (1A) and syn-(S)-streptorubin (1B). Atropisomerism is a dynamic phenomenon with a potentially nonequilibrium population of isomers, and accordingly the measured chiroptical responses may vary with time, concentration, temperature, and the anion of the salts used. Streptorubin also has the potential to form stacked homodimers for which the optical rotations measured at 589 nm can vary greatly due to the presence of ECD-active electronic transitions in this region. Chirality 27:745-751, 2015. (c) 2015 Wiley Periodicals, Inc.

Original language	English
Pages (from-to)	745-751
Number of pages	7
Journal	Chirality
Volume	27
Issue number	0899-0042
DOIs	https://doi.org/10.1002/chir.22486
Publication status	Published - Oct 2015

Keywords

prodigiosins
streptorubin B
atropisomers
pseudoenantiomers
chiroptical properties
ORP
ECD
VCD
TDDFT calculations

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@article{04e796097e724f70a0640a471c51ba4f,

title = "Chiroptical Properties of Streptorubin B: The Synergy Between Theory and Experiment",

abstract = "Analysis of the calculated and measured optical rotation (OR) together with other calculated chiroptical properties such as electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of the prodigiosin alkaloid streptorubin B shows that these are dominated by the pseudoenantiomeric atropisomers anti-(S)-streptorubin B (1A) and syn-(S)-streptorubin (1B). Atropisomerism is a dynamic phenomenon with a potentially nonequilibrium population of isomers, and accordingly the measured chiroptical responses may vary with time, concentration, temperature, and the anion of the salts used. Streptorubin also has the potential to form stacked homodimers for which the optical rotations measured at 589 nm can vary greatly due to the presence of ECD-active electronic transitions in this region. Chirality 27:745-751, 2015. (c) 2015 Wiley Periodicals, Inc.",

keywords = "prodigiosins, streptorubin B, atropisomers, pseudoenantiomers, chiroptical properties, ORP, ECD, VCD, TDDFT calculations",

author = "Andrade, {Marta Morais Saraiva de} and Silva, {Vanessa S.} and Louren{\c c}o, {Ana Maria Ferreira da Costa} and Lobo, {Ana Maria F{\'e}lix Trindade} and Rzepa, {Henry S.}",

note = "Sem PDF. Fundacao para a Ciencia e Tecnologia (PTDC/QUI-QUI/101813/2008 - MarinatProd-XXI; PEst-C/EQB/LA0006/2013)",

year = "2015",

month = oct,

doi = "10.1002/chir.22486",

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T2 - The Synergy Between Theory and Experiment

AU - Andrade, Marta Morais Saraiva de

AU - Silva, Vanessa S.

AU - Lourenço, Ana Maria Ferreira da Costa

AU - Lobo, Ana Maria Félix Trindade

AU - Rzepa, Henry S.

N1 - Sem PDF. Fundacao para a Ciencia e Tecnologia (PTDC/QUI-QUI/101813/2008 - MarinatProd-XXI; PEst-C/EQB/LA0006/2013)

PY - 2015/10

Y1 - 2015/10

N2 - Analysis of the calculated and measured optical rotation (OR) together with other calculated chiroptical properties such as electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of the prodigiosin alkaloid streptorubin B shows that these are dominated by the pseudoenantiomeric atropisomers anti-(S)-streptorubin B (1A) and syn-(S)-streptorubin (1B). Atropisomerism is a dynamic phenomenon with a potentially nonequilibrium population of isomers, and accordingly the measured chiroptical responses may vary with time, concentration, temperature, and the anion of the salts used. Streptorubin also has the potential to form stacked homodimers for which the optical rotations measured at 589 nm can vary greatly due to the presence of ECD-active electronic transitions in this region. Chirality 27:745-751, 2015. (c) 2015 Wiley Periodicals, Inc.

AB - Analysis of the calculated and measured optical rotation (OR) together with other calculated chiroptical properties such as electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of the prodigiosin alkaloid streptorubin B shows that these are dominated by the pseudoenantiomeric atropisomers anti-(S)-streptorubin B (1A) and syn-(S)-streptorubin (1B). Atropisomerism is a dynamic phenomenon with a potentially nonequilibrium population of isomers, and accordingly the measured chiroptical responses may vary with time, concentration, temperature, and the anion of the salts used. Streptorubin also has the potential to form stacked homodimers for which the optical rotations measured at 589 nm can vary greatly due to the presence of ECD-active electronic transitions in this region. Chirality 27:745-751, 2015. (c) 2015 Wiley Periodicals, Inc.

KW - prodigiosins

KW - streptorubin B

KW - atropisomers

KW - pseudoenantiomers

KW - chiroptical properties

KW - ORP

KW - ECD

KW - VCD

KW - TDDFT calculations

U2 - 10.1002/chir.22486

DO - 10.1002/chir.22486

M3 - Article

C2 - 26316261

SN - 0899-0042

VL - 27

SP - 745

EP - 751

JO - Chirality

JF - Chirality

IS - 0899-0042

ER -

Chiroptical Properties of Streptorubin B: The Synergy Between Theory and Experiment

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Keywords

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