Synthesis and utilization of 13C and 15N backbone-labeled proline: NMR study of synthesized oxytocin with backbone-labeled C-terminal tripeptide amide |
| |
Authors: | M Budαěšínský U Ragnarsson L Lankiewicz L Grehn J Slaninová J Hlaváček |
| |
Institution: | (1) Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic;(2) Department of Biochemistry, University of Uppsala, Biomedical Center, Uppsala, Sweden |
| |
Abstract: | Summary. 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 β-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. |
| |
Keywords: | : Labeled proline – Oxytocin isotopomer – Peptide synthesis – Segment condensation – Protected tocinoic acid – Bioassay – NMR study |
本文献已被 PubMed SpringerLink 等数据库收录! |
|