Steroselective synthesis and application of L-( sup 15 N) amino acids

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We have developed two general approaches to the stereoselective synthesis of {sup 15}N- and {sup 13}C-labeled amino acids. First, labeled serine, biosynthesized using the methylotrophic bacterium M. extorquens AM1, serves as a chiral precursor for the synthesis of other amino acids. For example, pyridoxal phosphate enzymes can be used for the conversion of L-({alpha}-{sup 15}N)serine to L-({alpha}-{sup 15}N)tyrosine, L-({alpha}-{sup 15}N)tryptophan, and L-({alpha}-{sup 15}N)cysteine. In the second approach, developed by Oppolzer and Tamura, an electrophilic amination'' reagent, 1-chloro-1-nitrosocyclohexane, was used to convert chiral enolates into L-{alpha}-amino acids. We prepared 1-chloro-1-({sup 15}N) nitrosocyclohexane and used it to aminate chiral enolates to produce … continued below

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Unkefer, C.J. (Los Alamos National Lab., NM (United States)) & Lodwig, S.N. (Centralia Coll., WA (United States). Div. of Science) January 1, 1991.

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We have developed two general approaches to the stereoselective synthesis of {sup 15}N- and {sup 13}C-labeled amino acids. First, labeled serine, biosynthesized using the methylotrophic bacterium M. extorquens AM1, serves as a chiral precursor for the synthesis of other amino acids. For example, pyridoxal phosphate enzymes can be used for the conversion of L-({alpha}-{sup 15}N)serine to L-({alpha}-{sup 15}N)tyrosine, L-({alpha}-{sup 15}N)tryptophan, and L-({alpha}-{sup 15}N)cysteine. In the second approach, developed by Oppolzer and Tamura, an electrophilic amination'' reagent, 1-chloro-1-nitrosocyclohexane, was used to convert chiral enolates into L-{alpha}-amino acids. We prepared 1-chloro-1-({sup 15}N) nitrosocyclohexane and used it to aminate chiral enolates to produce L-({alpha}-{sup 15}N)amino acids. The stereoselectivity of this scheme using the Oppolzer sultam chiral auxiliary is remarkable, producing enantiomer ratios of 200 to 1. 22 refs., 4 figs.

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7 pages

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OSTI; NTIS; GPO Dep.

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  • 4. international symposium on the synthesis and applications of isotopes and isotopically labeled compounds, Toronto (Canada), 3 Sep 1991

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  • Other: DE92002373
  • Report No.: LA-UR-91-3296
  • Report No.: CONF-9109287--2
  • Grant Number: W-7405-ENG-36
  • Office of Scientific & Technical Information Report Number: 5047141
  • Archival Resource Key: ark:/67531/metadc1057561

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  • January 1, 1991

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Unkefer, C.J. (Los Alamos National Lab., NM (United States)) & Lodwig, S.N. (Centralia Coll., WA (United States). Div. of Science). Steroselective synthesis and application of L-( sup 15 N) amino acids, article, January 1, 1991; New Mexico. (https://digital.library.unt.edu/ark:/67531/metadc1057561/: accessed July 16, 2024), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT Libraries Government Documents Department.

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