Synthesis of Psychrophilin E

Sarah T Y Ngen; Harveen Kaur; Paul A Hume; Daniel P Furkert; Margaret A Brimble

doi:10.1021/acs.joc.6b01369

Synthesis of Psychrophilin E

J Org Chem. 2016 Sep 2;81(17):7635-43. doi: 10.1021/acs.joc.6b01369. Epub 2016 Jul 28.

Authors

Sarah T Y Ngen^{1

2}, Harveen Kaur^{1

2}, Paul A Hume^{1

2}, Daniel P Furkert^{1

2}, Margaret A Brimble^{1

2}

Affiliations

¹ School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland, New Zealand.
² Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3 Symonds Street, Auckland, New Zealand.

PMID: 27442351
DOI: 10.1021/acs.joc.6b01369

Abstract

The first total synthesis of psychrophilin E, a potent antiproliferative cyclic tripeptide isolated from Aspergillus versicolor ZLN-60, is reported herein. Key features of the synthesis include the installation of an amide bond between the indole-nitrogen of tryptophan and an anthranilic acid residue, and a high yielding macrolactamization of the linear tripeptide to the desired macrocycle.

MeSH terms

Aspergillus / chemistry
Indoles / chemistry
Nitrogen / chemistry
Nuclear Magnetic Resonance, Biomolecular
Peptides, Cyclic / chemical synthesis*
Peptides, Cyclic / chemistry
Peptides, Cyclic / isolation & purification
Spectrometry, Mass, Electrospray Ionization
Tryptophan / chemistry
ortho-Aminobenzoates / chemistry

Substances

Indoles
Peptides, Cyclic
ortho-Aminobenzoates
psychrophilin E
anthranilic acid
Tryptophan
Nitrogen