Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades

Grayson J. Ford; Nico Kress; Ashley P. Mattey; Lorna J. Hepworth; Christopher R. Baldwin; James R. Marshall; Lisa S. Seibt; Min Huang; William R. Birmingham; Nicholas J. Turner; Sabine L. Flitsch

doi:10.1039/d0cc02976a

Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades

Grayson J. Ford, Nico Kress, Ashley P. Mattey, Lorna J. Hepworth, Christopher R. Baldwin, James R. Marshall, Lisa S. Seibt, Min Huang, William R. Birmingham, Nicholas J. Turner, Sabine L. Flitsch

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Abstract

Multi-enzyme cascades utilising variants of galactose oxidase and imine reductase led to the successful conversion of N-Cbz-protected l-ornithinol and l-lysinol to l-3-N-Cbz-aminopiperidine and l-3-N-Cbz-aminoazepane respectively, in up to 54% isolated yield. Streamlining the reactions into one-pot prevented potential racemisation of key labile intermediates and led to products with high enantiopurity.

Original language	English
Pages (from-to)	7949-7952
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	57
DOIs	https://doi.org/10.1039/d0cc02976a
Publication status	Published - 21 Jul 2020

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title = "Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades",

abstract = "Multi-enzyme cascades utilising variants of galactose oxidase and imine reductase led to the successful conversion of N-Cbz-protected l-ornithinol and l-lysinol to l-3-N-Cbz-aminopiperidine and l-3-N-Cbz-aminoazepane respectively, in up to 54% isolated yield. Streamlining the reactions into one-pot prevented potential racemisation of key labile intermediates and led to products with high enantiopurity.",

author = "Ford, {Grayson J.} and Nico Kress and Mattey, {Ashley P.} and Hepworth, {Lorna J.} and Baldwin, {Christopher R.} and Marshall, {James R.} and Seibt, {Lisa S.} and Min Huang and Birmingham, {William R.} and Turner, {Nicholas J.} and Flitsch, {Sabine L.}",

year = "2020",

month = jul,

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doi = "10.1039/d0cc02976a",

language = "English",

volume = "56",

pages = "7949--7952",

journal = "Chemical Communications",

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TY - JOUR

T1 - Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades

AU - Ford, Grayson J.

AU - Kress, Nico

AU - Mattey, Ashley P.

AU - Hepworth, Lorna J.

AU - Baldwin, Christopher R.

AU - Marshall, James R.

AU - Seibt, Lisa S.

AU - Huang, Min

AU - Birmingham, William R.

AU - Turner, Nicholas J.

AU - Flitsch, Sabine L.

PY - 2020/7/21

Y1 - 2020/7/21

N2 - Multi-enzyme cascades utilising variants of galactose oxidase and imine reductase led to the successful conversion of N-Cbz-protected l-ornithinol and l-lysinol to l-3-N-Cbz-aminopiperidine and l-3-N-Cbz-aminoazepane respectively, in up to 54% isolated yield. Streamlining the reactions into one-pot prevented potential racemisation of key labile intermediates and led to products with high enantiopurity.

AB - Multi-enzyme cascades utilising variants of galactose oxidase and imine reductase led to the successful conversion of N-Cbz-protected l-ornithinol and l-lysinol to l-3-N-Cbz-aminopiperidine and l-3-N-Cbz-aminoazepane respectively, in up to 54% isolated yield. Streamlining the reactions into one-pot prevented potential racemisation of key labile intermediates and led to products with high enantiopurity.

U2 - 10.1039/d0cc02976a

DO - 10.1039/d0cc02976a

M3 - Article

C2 - 32531011

SN - 1364-548X

VL - 56

SP - 7949

EP - 7952

JO - Chemical Communications

JF - Chemical Communications

IS - 57

ER -

Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades

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