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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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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. |
format | Online Article Text |
id | pubmed-3648273 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT englichulrich metacridamidebmethanold4monosolvate AT krasnoffstuartb metacridamidebmethanold4monosolvate |