Development of a Biocatalytic Aerobic Oxidation for the Manufacturing Route to Islatravir
Megan H Shaw
1
,
Anna Fryszkowska
1
,
Oscar Alvizo
2
,
Ilana Attadgie
1
,
Margie Borra‐Garske
2
,
Margie Borra Garske
2
,
Paul N Devine
1
,
Paul N. PAUL E. DEVINE (2)
1
,
Da Duan
2
,
Shane T Grosser
1
,
Jacob H Forstater
1
,
Gregory J. Hughes
1
,
Graham J. Hughes
1
,
Kevin M. Maloney
1
,
Eric L. Margelefsky
1
,
Keith Mattern
1
,
Margaret T. Miller
1
,
Christopher C Nawrat
1
,
Jovana Nazor
2
,
Peter Orth
3
,
Claire M. Ouimet
4
,
Sandra A Robaire
1
,
Serge Ruccolo
1
,
Erica L. Schwalm
4
,
Deeptak Verma
3
,
Li Xiao
3
,
Victoria Zhang
1
,
Victoria X Zhang
1
1
Process Research & Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
|
2
Codexis, Inc., 200 Penobscot Drive, Redwood City, California 94063, United States
|
3
Discovery Chemistry, Merck & Co., Inc., Rahway, New Jersey 07065, United States
|
4
Analytical Research & Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
|
Publication type: Journal Article
Publication date: 2024-08-14
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Abstract
Biocatalytic oxidations have the potential to address many synthetic challenges, enabling the selective synthesis of chiral intermediates, such as carbonyl compounds, alcohols, or amines. The use of oxygen-dependent enzymes can dramatically reduce the environmental footprint of redox transformations at the manufacturing scale. Here, as part of the biocatalytic cascade to the anti-HIV investigational drug islatravir (1), we describe the development of an aerobic oxidation process delivering (R)-ethynylglyceraldehyde-3-phosphate (3) using an evolved galactose oxidase enzyme. Integrated enzyme and reaction engineering were critical for achieving a robust, high-yielding oxidation performed at pilot-plant scale (>20 kg, 90% yield).
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10
Total citations:
10
Citations from 2024:
9
(90%)
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GOST
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Shaw M. H. et al. Development of a Biocatalytic Aerobic Oxidation for the Manufacturing Route to Islatravir // Organic Process Research and Development. 2024. Vol. 28. No. 9. pp. 3545-3559.
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Shaw M. H., Fryszkowska A., Alvizo O., Attadgie I., Borra‐Garske M., Borra Garske M., Devine P. N., PAUL E. DEVINE (2) P. N., Duan D., Grosser S. T., Forstater J. H., Hughes G. J., Hughes G. J., Maloney K. M., Margelefsky E. L., Mattern K., Miller M. T., Nawrat C. C., Nazor J., Orth P., Ouimet C. M., Robaire S. A., Ruccolo S., Schwalm E. L., Verma D., Xiao L., Zhang V., Zhang V. X. Development of a Biocatalytic Aerobic Oxidation for the Manufacturing Route to Islatravir // Organic Process Research and Development. 2024. Vol. 28. No. 9. pp. 3545-3559.
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TY - JOUR
DO - 10.1021/acs.oprd.4c00075
UR - https://pubs.acs.org/doi/10.1021/acs.oprd.4c00075
TI - Development of a Biocatalytic Aerobic Oxidation for the Manufacturing Route to Islatravir
T2 - Organic Process Research and Development
AU - Shaw, Megan H
AU - Fryszkowska, Anna
AU - Alvizo, Oscar
AU - Attadgie, Ilana
AU - Borra‐Garske, Margie
AU - Borra Garske, Margie
AU - Devine, Paul N
AU - PAUL E. DEVINE (2), Paul N.
AU - Duan, Da
AU - Grosser, Shane T
AU - Forstater, Jacob H
AU - Hughes, Gregory J.
AU - Hughes, Graham J.
AU - Maloney, Kevin M.
AU - Margelefsky, Eric L.
AU - Mattern, Keith
AU - Miller, Margaret T.
AU - Nawrat, Christopher C
AU - Nazor, Jovana
AU - Orth, Peter
AU - Ouimet, Claire M.
AU - Robaire, Sandra A
AU - Ruccolo, Serge
AU - Schwalm, Erica L.
AU - Verma, Deeptak
AU - Xiao, Li
AU - Zhang, Victoria
AU - Zhang, Victoria X
PY - 2024
DA - 2024/08/14
PB - American Chemical Society (ACS)
SP - 3545-3559
IS - 9
VL - 28
SN - 1083-6160
SN - 1520-586X
ER -
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@article{2024_Shaw,
author = {Megan H Shaw and Anna Fryszkowska and Oscar Alvizo and Ilana Attadgie and Margie Borra‐Garske and Margie Borra Garske and Paul N Devine and Paul N. PAUL E. DEVINE (2) and Da Duan and Shane T Grosser and Jacob H Forstater and Gregory J. Hughes and Graham J. Hughes and Kevin M. Maloney and Eric L. Margelefsky and Keith Mattern and Margaret T. Miller and Christopher C Nawrat and Jovana Nazor and Peter Orth and Claire M. Ouimet and Sandra A Robaire and Serge Ruccolo and Erica L. Schwalm and Deeptak Verma and Li Xiao and Victoria Zhang and Victoria X Zhang},
title = {Development of a Biocatalytic Aerobic Oxidation for the Manufacturing Route to Islatravir},
journal = {Organic Process Research and Development},
year = {2024},
volume = {28},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://pubs.acs.org/doi/10.1021/acs.oprd.4c00075},
number = {9},
pages = {3545--3559},
doi = {10.1021/acs.oprd.4c00075}
}
Cite this
MLA
Copy
Shaw, Megan H., et al. “Development of a Biocatalytic Aerobic Oxidation for the Manufacturing Route to Islatravir.” Organic Process Research and Development, vol. 28, no. 9, Aug. 2024, pp. 3545-3559. https://pubs.acs.org/doi/10.1021/acs.oprd.4c00075.