Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

Nicoló Scalacci; Gary W. Black; Giulio Mattedi; Nicola L. Brown; Nicholas J. Turner; Daniele Castagnolo

doi:10.1021/acscatal.6b03081

Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

Nicoló Scalacci, Gary W. Black, Giulio Mattedi, Nicola L. Brown, Nicholas J. Turner, Daniele Castagnolo

Applied Sciences Department

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Abstract

A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis–aromatization sequence.

Original language	English
Pages (from-to)	1295-1300
Number of pages	6
Journal	ACS Catalysis
Volume	7
Issue number	2
Early online date	27 Dec 2016
DOIs	https://doi.org/10.1021/acscatal.6b03081
Publication status	Published - 3 Feb 2017

Keywords

biocatalysis
chemoenzymatic cascade
MAO-N
metathesis
pyrrole

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acscatal.6b03081

Scalacci et al - Unveiling the biocatalytic aromatizing activity of monoamine oxidases MAO-N and 6-HDNOAccepted author manuscript, 8.8 MB

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title = "Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles",

abstract = "A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis–aromatization sequence.",

keywords = "biocatalysis, chemoenzymatic cascade, MAO-N, metathesis, pyrrole",

author = "Nicol{\'o} Scalacci and Black, {Gary W.} and Giulio Mattedi and Brown, {Nicola L.} and Turner, {Nicholas J.} and Daniele Castagnolo",

year = "2017",

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doi = "10.1021/acscatal.6b03081",

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T1 - Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO

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AU - Scalacci, Nicoló

AU - Black, Gary W.

AU - Mattedi, Giulio

AU - Brown, Nicola L.

AU - Turner, Nicholas J.

AU - Castagnolo, Daniele

PY - 2017/2/3

Y1 - 2017/2/3

N2 - A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis–aromatization sequence.

AB - A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis–aromatization sequence.

KW - biocatalysis

KW - chemoenzymatic cascade

KW - MAO-N

KW - metathesis

KW - pyrrole

U2 - 10.1021/acscatal.6b03081

DO - 10.1021/acscatal.6b03081

M3 - Article

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SP - 1295

EP - 1300

JO - ACS Catalysis

JF - ACS Catalysis

IS - 2

ER -

Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

Abstract

Keywords

UN SDGs

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