Total Synthesis of Micrococcin P1 through Scalable Thiazole Forming Reactions of Cysteine Derivatives and Nitriles
Mitchell P Christy
1
,
Trevor Johnson
1
,
Clare D Mcnerlin
2
,
John Woodard
2
,
Andrew T. Nelson
3, 4
,
Bryant Lim
2
,
Tiffany L Hamilton
2
,
Kaitlyn M Freiberg
2
,
Dionicio Siegel
2
Publication type: Journal Article
Publication date: 2020-03-05
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
32134277
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Thiopeptides are a class of natural products with untapped therapeutic potential. To expand the methods available for the scaled production of these antibiotics, we report the laboratory synthesis of micrococcin P1 showcasing thiazole forming reactions of cysteine derivatives and nitriles followed by oxidation. In most instances, this thiazole forming sequence does not require chromatography and proved scalable. Using this approach, 199 mg of micrococcin P1 was generated in a single synthetic sequence.
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Metrics
21
Total citations:
21
Citations from 2025:
5
(23.81%)
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MLA
Cite this
GOST
Copy
Christy M. P. et al. Total Synthesis of Micrococcin P1 through Scalable Thiazole Forming Reactions of Cysteine Derivatives and Nitriles // Organic Letters. 2020. Vol. 22. No. 6. pp. 2365-2370.
GOST all authors (up to 50)
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Christy M. P., Johnson T., Mcnerlin C. D., Woodard J., Nelson A. T., Lim B., Hamilton T. L., Freiberg K. M., Siegel D. Total Synthesis of Micrococcin P1 through Scalable Thiazole Forming Reactions of Cysteine Derivatives and Nitriles // Organic Letters. 2020. Vol. 22. No. 6. pp. 2365-2370.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.0c00202
UR - https://doi.org/10.1021/acs.orglett.0c00202
TI - Total Synthesis of Micrococcin P1 through Scalable Thiazole Forming Reactions of Cysteine Derivatives and Nitriles
T2 - Organic Letters
AU - Christy, Mitchell P
AU - Johnson, Trevor
AU - Mcnerlin, Clare D
AU - Woodard, John
AU - Nelson, Andrew T.
AU - Lim, Bryant
AU - Hamilton, Tiffany L
AU - Freiberg, Kaitlyn M
AU - Siegel, Dionicio
PY - 2020
DA - 2020/03/05
PB - American Chemical Society (ACS)
SP - 2365-2370
IS - 6
VL - 22
PMID - 32134277
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Christy,
author = {Mitchell P Christy and Trevor Johnson and Clare D Mcnerlin and John Woodard and Andrew T. Nelson and Bryant Lim and Tiffany L Hamilton and Kaitlyn M Freiberg and Dionicio Siegel},
title = {Total Synthesis of Micrococcin P1 through Scalable Thiazole Forming Reactions of Cysteine Derivatives and Nitriles},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.orglett.0c00202},
number = {6},
pages = {2365--2370},
doi = {10.1021/acs.orglett.0c00202}
}
Cite this
MLA
Copy
Christy, Mitchell P., et al. “Total Synthesis of Micrococcin P1 through Scalable Thiazole Forming Reactions of Cysteine Derivatives and Nitriles.” Organic Letters, vol. 22, no. 6, Mar. 2020, pp. 2365-2370. https://doi.org/10.1021/acs.orglett.0c00202.