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Metacridamide B methanol-d (4) monosolvate

The title compound, C(35)H(53)NO(5)·CH(3)OH {systematic name: (3S,6E,8S,9R,10E,12S,13S,14E,16S,17R)-3-benzyl-9,13-dihy­droxy-6,8,10,12,14,16-hexa­methyl-17-[(2S,4S)-4-methyl­hexan-2-yl]-1-oxa-4-aza­cyclo­hepta­deca-6,10,14-triene-2,5-dione methanol-d (4) monosolvate}, was extracted from conidia of t...

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Autores principales: Englich, Ulrich, Krasnoff, Stuart B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3648273/
https://www.ncbi.nlm.nih.gov/pubmed/23723893
http://dx.doi.org/10.1107/S1600536813009641
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author Englich, Ulrich
Krasnoff, Stuart B.
author_facet Englich, Ulrich
Krasnoff, Stuart B.
author_sort Englich, Ulrich
collection PubMed
description The title compound, C(35)H(53)NO(5)·CH(3)OH {systematic name: (3S,6E,8S,9R,10E,12S,13S,14E,16S,17R)-3-benzyl-9,13-dihy­droxy-6,8,10,12,14,16-hexa­methyl-17-[(2S,4S)-4-methyl­hexan-2-yl]-1-oxa-4-aza­cyclo­hepta­deca-6,10,14-triene-2,5-dione methanol-d (4) monosolvate}, was extracted from conidia of the fungus Metarhizium acridum. Crystals were obtained as a methanol-d (4) solvate. The tail part of the 4-methyl­hexan-2-yl group exhibits disorder over two positions, with an occupancy ratio of 0.682 (9):0.318 (9). The crystal structure confirms the absolute configuration of nine stereocenters determined previously for the acetyl­ated compound metacridamide A. In the crystal, the methanol-d4 mol­ecule is positioned close to the O atom in the carbonyl group of the peptide bond, forming an O—H⋯O hydrogen bond. It also forms an O—H⋯O hydrogen bond with an adjacent mol­ecule. N—H⋯O and O—H⋯O hydrogen bonds are observed between neighboring mol­ecules.
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spelling pubmed-36482732013-05-30 Metacridamide B methanol-d (4) monosolvate Englich, Ulrich Krasnoff, Stuart B. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(35)H(53)NO(5)·CH(3)OH {systematic name: (3S,6E,8S,9R,10E,12S,13S,14E,16S,17R)-3-benzyl-9,13-dihy­droxy-6,8,10,12,14,16-hexa­methyl-17-[(2S,4S)-4-methyl­hexan-2-yl]-1-oxa-4-aza­cyclo­hepta­deca-6,10,14-triene-2,5-dione methanol-d (4) monosolvate}, was extracted from conidia of the fungus Metarhizium acridum. Crystals were obtained as a methanol-d (4) solvate. The tail part of the 4-methyl­hexan-2-yl group exhibits disorder over two positions, with an occupancy ratio of 0.682 (9):0.318 (9). The crystal structure confirms the absolute configuration of nine stereocenters determined previously for the acetyl­ated compound metacridamide A. In the crystal, the methanol-d4 mol­ecule is positioned close to the O atom in the carbonyl group of the peptide bond, forming an O—H⋯O hydrogen bond. It also forms an O—H⋯O hydrogen bond with an adjacent mol­ecule. N—H⋯O and O—H⋯O hydrogen bonds are observed between neighboring mol­ecules. International Union of Crystallography 2013-04-17 /pmc/articles/PMC3648273/ /pubmed/23723893 http://dx.doi.org/10.1107/S1600536813009641 Text en © Englich and Krasnoff 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Englich, Ulrich
Krasnoff, Stuart B.
Metacridamide B methanol-d (4) monosolvate
title Metacridamide B methanol-d (4) monosolvate
title_full Metacridamide B methanol-d (4) monosolvate
title_fullStr Metacridamide B methanol-d (4) monosolvate
title_full_unstemmed Metacridamide B methanol-d (4) monosolvate
title_short Metacridamide B methanol-d (4) monosolvate
title_sort metacridamide b methanol-d (4) monosolvate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3648273/
https://www.ncbi.nlm.nih.gov/pubmed/23723893
http://dx.doi.org/10.1107/S1600536813009641
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