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Title: Stereoselective synthesis of stable-isotope-labeled amino acids

Abstract

For magnetic resonance and vibrational spectroscopies to reach their full potential, they must be used in combination with sophisticated site-specific stable isotope labeling of biological macromolecules. Labeled amino acids are required for the study of the structure and function of enzymes and proteins. Because there are 20 common amino acids, each with its own distinguishing chemistry, they remain a synthetic challenge. The Oppolzer chiral auxiliary provides a general tool with which to approach the synthesis of labeled amino acids. By using the Oppolzer auxiliary, amino acids can be constructed from several small molecules, which is ideal for stable isotope labeling. In addition to directing the stereochemistry at the {alpha}-carbon, the camphorsultam can be used for stereo-specific isotope labeling at prochiral centers in amino acids. By using the camphorsultam auxiliary we have the potential to synthesize virtually any isotopomer of all of the common amino acids.

Authors:
; ;  [1];  [2]
  1. Los Alamos National Laboratory, NM (United States)
  2. Centralia College, WA (United States)
Publication Date:
Research Org.:
Los Alamos National Lab., NM (United States)
OSTI Identifier:
83387
Report Number(s):
LA-12893-C; CONF-9403228-
ON: DE95012795; TRN: 95:004732-0018
Resource Type:
Conference
Resource Relation:
Conference: Stable isotope applications in biomolecular structure and mechanisms, Santa Fe, NM (United States), 27-31 Mar 1994; Other Information: PBD: Dec 1994; Related Information: Is Part Of Stable isotope applications in biomolecular structure and mechanisms. A meeting to bring together producers and users of stable-isotope-labeled compounds to assess current and future needs; Trewhella, J.; Cross, T.A.; Unkefer, C.J. [eds.]; PB: 382 p.
Country of Publication:
United States
Language:
English
Subject:
55 BIOLOGY AND MEDICINE, BASIC STUDIES; 40 CHEMISTRY; AMINO ACIDS; SYNTHESIS; LABELLING; ENZYMES; MOLECULAR STRUCTURE; PROTEINS; ISOTOPE APPLICATIONS; MAGNETIC RESONANCE; STEREOCHEMISTRY

Citation Formats

Unkefer, C.J., Martinez, R.A., Silks, L.A. III, and Lodwig, S.N.. Stereoselective synthesis of stable-isotope-labeled amino acids. United States: N. p., 1994. Web.
Unkefer, C.J., Martinez, R.A., Silks, L.A. III, & Lodwig, S.N.. Stereoselective synthesis of stable-isotope-labeled amino acids. United States.
Unkefer, C.J., Martinez, R.A., Silks, L.A. III, and Lodwig, S.N.. Thu . "Stereoselective synthesis of stable-isotope-labeled amino acids". United States. doi:. https://www.osti.gov/servlets/purl/83387.
@article{osti_83387,
title = {Stereoselective synthesis of stable-isotope-labeled amino acids},
author = {Unkefer, C.J. and Martinez, R.A. and Silks, L.A. III and Lodwig, S.N.},
abstractNote = {For magnetic resonance and vibrational spectroscopies to reach their full potential, they must be used in combination with sophisticated site-specific stable isotope labeling of biological macromolecules. Labeled amino acids are required for the study of the structure and function of enzymes and proteins. Because there are 20 common amino acids, each with its own distinguishing chemistry, they remain a synthetic challenge. The Oppolzer chiral auxiliary provides a general tool with which to approach the synthesis of labeled amino acids. By using the Oppolzer auxiliary, amino acids can be constructed from several small molecules, which is ideal for stable isotope labeling. In addition to directing the stereochemistry at the {alpha}-carbon, the camphorsultam can be used for stereo-specific isotope labeling at prochiral centers in amino acids. By using the camphorsultam auxiliary we have the potential to synthesize virtually any isotopomer of all of the common amino acids.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Thu Dec 01 00:00:00 EST 1994},
month = {Thu Dec 01 00:00:00 EST 1994}
}

Conference:
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