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Crystal and Molecular Structure of S-Deoxo[Ile^3]amaninamide: A Synthetic Analog of Amanita Toxins

Shoham, G. and Rees, D. C. and Lipscomb, W. N. and Zanotti, G. and Wieland, Th. (1984) Crystal and Molecular Structure of S-Deoxo[Ile^3]amaninamide: A Synthetic Analog of Amanita Toxins. Journal of the American Chemical Society, 106 (16). pp. 4606-4615. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20150210-095029990

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Abstract

The crystal structure of S-deoxo[Ile^3]amaninamide, a nontoxic synthetic derivative of the Amanita phalloides mushroom toxins (amatoxins), has been determined by single-crystal X-ray diffraction. The crystals are monoclinic, space group P2_1, with 2 formula units per unit cell. Cell dimensions are a = 12.147 Å, b = 11.250 Å, c = 19.267 Å, and (β = 92.41°. The structure was determined by molecular replacement methods and refined by least-squares techniques to a final R value of 0.065 for 3894 independent observations. Six intramolecular hydrogen bonds hold the bicyclic octapeptide in a compact conformation, which is very similar to the conformation of the naturally occurring (and toxic) amatoxin, (β-amanitin. The study demonstrates that the 30-fold reduction in binding affinity to RNA polymerase B of the title amatoxin, and probably of most of the other amatoxin analogues with altered side chain 3, is not due to alteration of backbone conformation. The three water molecules and two ethanol molecules, crystallized with the amatoxin, form a strong and extensive intermolecular hydrogen-bonding system.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja00328a051 DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00328a051PublisherArticle
ORCID:
AuthorORCID
Rees, D. C.0000-0003-4073-1185
Additional Information:© 1984 by the American Chemical Society. Received December 22, 1983. We thank R. Dumas for technical help in formatting the manuscript, the National Institutes of Health (Grant GM06920) for support, and the National Science Foundation (Grant PCM 77-1398) for initial support of the computational laboratory.
Funders:
Funding AgencyGrant Number
NIHGM06920
NSFPCM 77-1398
Issue or Number:16
Record Number:CaltechAUTHORS:20150210-095029990
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150210-095029990
Official Citation:Crystal and molecular structure of S-deoxo[Ile3]amaninamide: a synthetic analog of Amanita toxins G. Shoham, D. C. Rees, W. N. Lipscomb, G. Zanotti, and T. Wieland Journal of the American Chemical Society 1984 106 (16), 4606-4615
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ID Code:54642
Collection:CaltechAUTHORS
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Deposited On:10 Feb 2015 18:06
Last Modified:03 Oct 2019 07:59

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