TY - JOUR
T1 - Tandem one-pot biocatalytic oxidation and Wittig reaction in water
AU - Wahart, Alice J. C.
AU - Beardmore, Liam N. D.
AU - Field, Robert A.
AU - Cosgrove, Sebastian C.
AU - Miller, Gavin J.
N1 - Data Availability Statement: The data underlying this study are available in the published article and its Supporting Information.
Funding Information: UK Research and Innovation (UKRI) (Future Leaders Fellowship, MR/T019522/1) is thanked for project grant funding to G.J.M. Keele University is thanked for Ph.D. funding to A.J.C.W. and L.N.D.B. We also thank the EPSRC UK National Mass Spectrometry Facility (NMSF) at Swansea University.
PY - 2024/8/9
Y1 - 2024/8/9
N2 - We explore biocatalytic aldehyde generation under aqueous conditions, concomitantly delivering access to a one-pot Wittig reaction using stabilized phosphoranes and granting diverse alkene products. Using a recombinant choline oxidase mutant, we first undertake biocatalytic alcohol oxidation across a range of functional aliphatic primary alcohols, demonstrating a remarkable substrate tolerance for this enzyme, including chloride, bromide, azide, S-methyl, and alkynyl groups. Following this, we extend capability and deliver a practicable milligram-scale one-pot Wittig reaction in water.
AB - We explore biocatalytic aldehyde generation under aqueous conditions, concomitantly delivering access to a one-pot Wittig reaction using stabilized phosphoranes and granting diverse alkene products. Using a recombinant choline oxidase mutant, we first undertake biocatalytic alcohol oxidation across a range of functional aliphatic primary alcohols, demonstrating a remarkable substrate tolerance for this enzyme, including chloride, bromide, azide, S-methyl, and alkynyl groups. Following this, we extend capability and deliver a practicable milligram-scale one-pot Wittig reaction in water.
UR - https://www.scopus.com/pages/publications/85199955198
U2 - 10.1021/acs.orglett.4c02201
DO - 10.1021/acs.orglett.4c02201
M3 - Article
C2 - 39075662
AN - SCOPUS:85199955198
SN - 1523-7060
VL - 26
SP - 6642
EP - 6646
JO - Organic Letters
JF - Organic Letters
IS - 31
ER -