Synthetic Marine Sponge Collagen by Late-Stage Dihydroxylation

Christoph Priem; Armin Geyer

doi:10.1021/acs.orglett.7b03525

Synthetic Marine Sponge Collagen by Late-Stage Dihydroxylation

Org Lett. 2018 Jan 5;20(1):162-165. doi: 10.1021/acs.orglett.7b03525. Epub 2017 Dec 15.

Authors

Christoph Priem¹, Armin Geyer¹

Affiliation

¹ Department of Chemistry, Philipps-Universität Marburg , Hans-Meerwein-Straße 4, 35032 Marburg, Germany.

PMID: 29244519
DOI: 10.1021/acs.orglett.7b03525

Abstract

Based on the observation that an increased substrate size is paralleled by an enhanced diastereoselectivity, a late-stage dihydroxylation protocol toward the 21mer CMP (collagen model peptide) Ac-(Pro-Hyp-Gly)₃-Pro-Dyp-Gly-(Pro-Hyp-Gly)₃-NH₂ is presented. C3 and C4 hydroxylation have a converse effect on the triple-helical stability of collagen. Their combined influence on the melting temperature was studied by NMR spectroscopy.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acid Sequence
Animals
Circular Dichroism
Collagen / chemistry*
Peptides
Porifera
Protein Conformation
Protein Structure, Secondary

Substances

Peptides
Collagen