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Synthesis and Structural Revision of Glyphaeaside C

Journal Article


Abstract


  • The iminosugar core of natural glyphaeaside C, originally assigned as a derivative of the piperidine natural product 1-deoxynojirimycin (DNJ), has been revised as a derivative of 2,5-dideoxy-2,5-imino-l-mannitol (l-DMDP) by the total synthesis of its enantiomer. This revised l-DMDP-derived configuration is the first of its kind to be observed in nature. The prepared iminosugars displayed the nanomolar inhibition of bovine liver β-glucosidase and β-galactosidase.

Publication Date


  • 2021

Citation


  • Byatt, B. J., Kato, A., & Pyne, S. G. (2021). Synthesis and Structural Revision of Glyphaeaside C. Organic Letters, 23(10), 4029-4033. doi:10.1021/acs.orglett.1c01248

Scopus Eid


  • 2-s2.0-85106502287

Start Page


  • 4029

End Page


  • 4033

Volume


  • 23

Issue


  • 10

Abstract


  • The iminosugar core of natural glyphaeaside C, originally assigned as a derivative of the piperidine natural product 1-deoxynojirimycin (DNJ), has been revised as a derivative of 2,5-dideoxy-2,5-imino-l-mannitol (l-DMDP) by the total synthesis of its enantiomer. This revised l-DMDP-derived configuration is the first of its kind to be observed in nature. The prepared iminosugars displayed the nanomolar inhibition of bovine liver β-glucosidase and β-galactosidase.

Publication Date


  • 2021

Citation


  • Byatt, B. J., Kato, A., & Pyne, S. G. (2021). Synthesis and Structural Revision of Glyphaeaside C. Organic Letters, 23(10), 4029-4033. doi:10.1021/acs.orglett.1c01248

Scopus Eid


  • 2-s2.0-85106502287

Start Page


  • 4029

End Page


  • 4033

Volume


  • 23

Issue


  • 10