Synthetic Marine Sponge Collagen by Late-Stage Dihydroxylation

Synthetic Marine Sponge Collagen by Late-Stage Dihydroxylation

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 effe...

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Veröffentlicht in:Organic letters 2018-01, Vol.20 (1), p.162-165
Hauptverfasser: Priem, Christoph, Geyer, Armin
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03525