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Solid‐state circular dichroism and hydrogen bonding: Absolute configuration of massarigenin A from Microsphaeropsis sp
Author(s) -
Hussain Hidayat,
Ahmed Ishtiaq,
Schulz Barbara,
Draeger Siegfried,
Flörke Ulrich,
Pescitelli Gennaro,
Krohn Karsten
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20985
Subject(s) - chemistry , absolute configuration , circular dichroism , hydrogen bond , crystallography , intermolecular force , vibrational circular dichroism , time dependent density functional theory , spectroscopy , density functional theory , crystal structure , magnetic circular dichroism , spectral line , stereochemistry , computational chemistry , molecule , organic chemistry , physics , quantum mechanics , astronomy
Massarigenin A ( 1 ) and papyracillic acids A ( 2 ) and B ( 3 ) were isolated from the endophytic fungus Microsphaeropsis sp. Their structures were elucidated by multidimensional nuclear magnetic resonance spectroscopy; the structure of massarigenin A ( 1 ) was also confirmed by X‐ray crystallography. The absolute configuration of massarigenin A ( 1 ) was established by means of circular dichroism (CD) spectroscopy and time‐dependent density functional theory (TDDFT) calculations. The impact of intermolecular hydrogen bonds detected in the crystal packing of 1 on CD spectra measured in the solid state was also investigated. Chirality, 2011. © 2011 Wiley‐Liss, Inc.
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