Modified Synthesis of the Peptidomimetic Natriuretic Peptide Receptor-C Antagonist M372049

Authors

Jacob Porter, Marquette University
Sergey V. Lindeman, Marquette UniversityFollow
Chris Dockendorff, Marquette UniversityFollow

Document Type

Article

Language

eng

Publication Date

3-19-2020

Publisher

Elsevier

Source Publication

Tetrahedron Letters

Source ISSN

0040-4039

Abstract

The Natriuretic Peptide Receptors (NPRs) regulate vascular sodium levels and have been of significant interest for the potential treatment of hypertension and related cardiovascular complications. The peptidomimetic antagonist M372049 is a valuable probe for the study of NPR-C signaling, unfortunately it is presently not commercially available. Described is a detailed protocol for its synthesis that does not require specialized apparatus and builds upon a prior patent from Veale and colleagues. Key steps include a base-mediated lactam formation and a solid-supported peptide synthetic sequence. An X-ray crystal structure of a key lactam intermediate was obtained to confirm the structure and relative stereochemistry of the compound.

Comments

Accepted version. Tetrahedron Letters, Vol. 61, No. 12 (March 19, 2020): 151654. DOI. © 2020 Elsevier. Used with permission.

Recommended Citation

Porter, Jacob; Lindeman, Sergey V.; and Dockendorff, Chris, "Modified Synthesis of the Peptidomimetic Natriuretic Peptide Receptor-C Antagonist M372049" (2020). Chemistry Faculty Research and Publications. 1005.
https://epublications.marquette.edu/chem_fac/1005