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Phosphothreonine as a catalytic residue in peptide-mediated asymmetric transfer hydrogenations of 8-aminoquinolines.

ABSTRACT: Phosphothreonine (pThr) was found to constitute a new class of chiral phosphoric acid (CPA) catalyst upon insertion into peptides. To demonstrate the potential of these phosphopeptides as asymmetric catalysts, enantioselective transfer hydrogenations of a previously underexplored substrate class for CPA-catalyzed reductions were carried out. pThr-containing peptides lead to the observation of enantioselectivities of up to 94:6 e.r. with 2-substituted quinolines containing C8-amino functionality. NMR studies indicate that hydrogen-bonding interactions promote strong complexation between substrates and a rigid ?-turn catalyst.

SUBMITTER: Shugrue CR

PROVIDER: S-EPMC4628550 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Phosphothreonine as a catalytic residue in peptide-mediated asymmetric transfer hydrogenations of 8-aminoquinolines.

Shugrue Christopher R CR Miller Scott J SJ

Angewandte Chemie (International ed. in English) 20150805 38

Phosphothreonine (pThr) was found to constitute a new class of chiral phosphoric acid (CPA) catalyst upon insertion into peptides. To demonstrate the potential of these phosphopeptides as asymmetric catalysts, enantioselective transfer hydrogenations of a previously underexplored substrate class for CPA-catalyzed reductions were carried out. pThr-containing peptides lead to the observation of enantioselectivities of up to 94:6 e.r. with 2-substituted quinolines containing C8-amino functionality. ...[more]

PMID: 26246129

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