Proteinogenic amino acids labelled with <sup>15</sup>N and/or <sup>13</sup>C for application in peptide synthesis: A short review with a comprehensive list of published derivatives

The 13C and 15N backbone-labeled proline was prepared using Oppolzer's method based on application of a sultam as chiral auxiliary. This isotopomer was used in the synthesis of the 13C, 15N backbone-labeled C-terminal tripeptide amide fragment of neurohypophyseal hormone oxytocin. Finally, this tripeptide amide was coupled by segment condensation with N-Boc- or N-Fmoc-tocinoic acid, followed by N-deprotection with TFA or piperidine. The labeled oxytocin exhibited biological activity identical with that of natural oxytocin. A detailed 1H, 13C and 15N NMR study confirmed the assigned oxytocin conformation containing a beta-turn in the cyclic part of the molecule, stabilized by H-bond(s) that can be perturbed by the C-terminal tripeptide amide moiety as indicated by comparison of NMR data for both the tocine ring in oxytocin and tocinoic acid.

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Proteinogenic amino acids labelled with ¹⁵N and/or ¹³C for application in peptide synthesis: A short review with a comprehensive list of published derivatives

Abstract: A review is given of the literature dealing with the most common protected derivatives of 15N- and/or 13C-labelled amino acids of interest in peptide synthesis. The list contains all such Boc-, Z- and Fmoc-amino acids as well as published methyl, ethyl, t-butyl and benzyl esters.

Cited by 4 publications

References 45 publications

ChemInform Abstract: Proteinogenic Amino Acids Labelled with 15N and/or 13C for Application in Peptide Synthesis: A Short Review with a Comprehensive List of Published Derivatives

ChemInform Abstract: Proteinogenic Amino Acids Labelled with 15N and/or 13C for Application in Peptide Synthesis: A Short Review with a Comprehensive List of Published Derivatives

Synthesis of amino acids selectively labelled with stable isotopes for application in peptide synthesis

Synthesis and utilization of 13C and 15N backbone-labeled proline: NMR study of synthesized oxytocin with backbone-labeled C-terminal tripeptide amide

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Proteinogenic amino acids labelled with 15N and/or 13C for application in peptide synthesis: A short review with a comprehensive list of published derivatives

Abstract: A review is given of the literature dealing with the most common protected derivatives of 15N- and/or 13C-labelled amino acids of interest in peptide synthesis. The list contains all such Boc-, Z- and Fmoc-amino acids as well as published methyl, ethyl, t-butyl and benzyl esters.

Cited by 4 publications

References 45 publications

ChemInform Abstract: Proteinogenic Amino Acids Labelled with 15N and/or 13C for Application in Peptide Synthesis: A Short Review with a Comprehensive List of Published Derivatives

ChemInform Abstract: Proteinogenic Amino Acids Labelled with 15N and/or 13C for Application in Peptide Synthesis: A Short Review with a Comprehensive List of Published Derivatives

Synthesis of amino acids selectively labelled with stable isotopes for application in peptide synthesis

Synthesis and utilization of 13C and 15N backbone-labeled proline: NMR study of synthesized oxytocin with backbone-labeled C-terminal tripeptide amide

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Product

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Proteinogenic amino acids labelled with ¹⁵N and/or ¹³C for application in peptide synthesis: A short review with a comprehensive list of published derivatives