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Assignment of the Nitrogen-15 Nuclear Magnetic Resonances of Biotin and Unequivocal Synthesis of (+)-[1-^(15)N]Biotin

Abe, Amy and Nee, Michael and Roberts, John D. and Wittenberg, Wayne L. and Leonard, Nelson J. (1981) Assignment of the Nitrogen-15 Nuclear Magnetic Resonances of Biotin and Unequivocal Synthesis of (+)-[1-^(15)N]Biotin. Journal of the American Chemical Society, 103 (16). pp. 4954-4956. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151006-073240480

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Abstract

(+)-Biotin (1) is an essential cofactor for several enzymes involving carboxylation and carbonyl-exchange reactiom It participates in the fixation, activation, and transfer of carbon dioxide by forming an N-carboxybiotin in which N1 was established as the point of attachment. The chemical reactivity of the the two ureido nitrogens of 1 is strikingly different. Thus, N1-and N3-acylated products in an 100:7 ratio resulted from the reaction of methyl chloroformate with biotin methyl ester. The low proportion of the N3 product was attributed to steric hindrance to the approach of the reagent to N3 because of the presence of the carboxylbutyl side chain. A similar argument was employed to account for the difference in exchange rates for the ureido protons with ethanol.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/ja00406a054DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00406a054PublisherArticle
Additional Information:© 1981 American Chemical Society. Received December 24, 1980. This work was supported at the University of Illinois by Research Grants CHE-76-23543 and CHE-79-22001 from the National Science Foundation and at the California Institute of Technology by the National Science Foundation and the US. Public Health Service, Research Grant GM-11072 from the Division of General Medical Sciences. We thank Dr. Janis Vasilevskis, Dr. Milan B. Uskoković, and Stanley D. Hutchings of the Chemical Research Department, Hoffmann-LaRoche, Inc., Nutley, NJ, for their generous help in materials and methodology.
Funders:
Funding AgencyGrant Number
NSFCHE-76-23543
NSFCHE-79-22001
U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry6345
Record Number:CaltechAUTHORS:20151006-073240480
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151006-073240480
Official Citation:Assignment of the nitrogen-15 nuclear magnetic resonances of biotin and unequivocal synthesis of (+)-[1-15N]biotin Amy Abe, Michael Nee, John D. Roberts, Wayne L. Wittenberg, and Nelson J. Leonard Journal of the American Chemical Society 1981 103 (16), 4954-4956 DOI: 10.1021/ja00406a054
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60795
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:06 Oct 2015 18:59
Last Modified:20 Sep 2016 20:56

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