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N-Phenylputrescine (NPP): A Natural Product Inspired Amine Donor for Biocatalysis

Journal article featured on front cover
Journal cover

The Campopiano and Lawrence groups have published a new amine donor for biocatalysis, inspired by nature and broadly applicable, which could open up greener and more sustainable alternatives to the metal-catalysed methods for synthesis of chiral amines that are currently used across the pharmaceutical, agrochemical and fine chemical industries. They also made the front cover of the journal!

This is the latest collaborative work to come out of the School of Chemistry powerhouse collaboration between the Campopiano and Lawrence groups.

The synthesis of amines is a key target in academic and industrial chemistry.Amines can be made from aldehydes and ketones.

As well as the traditional synthetic routes biocatalysts are being used to catalyse these conversions. Examples incldue the preparation of the billion dollar, blockbuster, anti-diabetic drug Sitagliptin by Merck and Codexis.

For this they use a transaminase (TA) biocatalyst and an amine donor. The amine donor is key since it controls the overall % yield of the reaction. Many amine donors are synthetic (e.g. isopropylamine) but we took inspiration from nature and designed a new donor, N-phenylputresine (NPP) based around a family of plant natural products (the incargranine alkaloids). The synthetic NPP displayed excellent properties across a range of TA-catalysed reactions giving us very high % conversions (this includes sitagliptin). We have already gifted NPP to many academic and industrial colleagues with the aim that they adopt it in their synthetic strategies.’

Professor Dominic Campopiano

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Friday, March 18, 2022