Comprehensive Strategies to Bicyclic Prolines: Applications in the Synthesis of Potent Arginase Inhibitors

Derun Li; Hongjun Zhang; Thomas W. Lyons; Min Lu; Abdelghani Achab; Qinglin Pu; Matthew Childers; Matthew J. Mitcheltree; Jialiang Wang; Theodore A. Martinot; Spencer E. McMinn; David L. Sloman; Anandan Palani; Adam Beard; Lisa Nogle; Symon Gathiaka; Josep Sauri; Hai-Young Kim; Donovon Adpressa; Peter Spacciapoli; J. Richard Miller; Rachel L. Palte; Charles A. Lesburg; Jared Cumming; Christian Fischer

doi:10.1021/acsmedchemlett.1c00258

Comprehensive Strategies to Bicyclic Prolines: Applications in the Synthesis of Potent Arginase Inhibitors

Derun Li, Hongjun Zhang, Thomas W. Lyons, Min Lu, Abdelghani Achab, Qinglin Pu, Matthew Childers, Matthew J. Mitcheltree, Jialiang Wang, Theodore A. Martinot, Spencer E. McMinn, David L. Sloman, Anandan Palani, Adam Beard, Lisa Nogle, Symon Gathiaka, Josep Sauri, Hai-Young Kim, Donovon Adpressa, Peter SpacciapoliJ. Richard Miller, Rachel L. Palte, Charles A. Lesburg, Jared Cumming, Christian Fischer

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Comprehensive synthetic strategies afforded a diverse set of structurally unique bicyclic proline-containing arginase inhibitors with a high degree of three-dimensionality. The analogs that favored the C gamma-exo conformation of the proline improved the arginase potency over the initial lead. The novel synthetic strategies reported here not only enable access to previously unknown stereochemically complex proline derivatives but also provide a foundation for the future synthesis of bicyclic proline analogs, which incorporate inherent three-dimensional character into building blocks, medicine, and catalysts and could have a profound impact on the conformation of proline-containing peptides and macrocycles.

Idioma original	Anglès
Pàgines (de-a)	1678-1688
Nombre de pàgines	11
Revista	Acs Medicinal Chemistry Letters
Volum	12
Número	11
Data online anticipada	13 d’oct. 2021
DOIs	https://doi.org/10.1021/acsmedchemlett.1c00258
Estat de la publicació	Publicada - 11 de nov. 2021
Publicat externament	Sí

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10.1021/acsmedchemlett.1c00258

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Li, D., Zhang, H., Lyons, T. W., Lu, M., Achab, A., Pu, Q., Childers, M., Mitcheltree, M. J., Wang, J., Martinot, T. A., McMinn, S. E., Sloman, D. L., Palani, A., Beard, A., Nogle, L., Gathiaka, S., Sauri, J., Kim, H.-Y., Adpressa, D., ... Fischer, C. (2021). Comprehensive Strategies to Bicyclic Prolines: Applications in the Synthesis of Potent Arginase Inhibitors. Acs Medicinal Chemistry Letters, 12(11), 1678-1688. https://doi.org/10.1021/acsmedchemlett.1c00258

@article{38778f14b20e4c798c5800c7b9b98d64,

title = "Comprehensive Strategies to Bicyclic Prolines: Applications in the Synthesis of Potent Arginase Inhibitors",

abstract = "Comprehensive synthetic strategies afforded a diverse set of structurally unique bicyclic proline-containing arginase inhibitors with a high degree of three-dimensionality. The analogs that favored the C gamma-exo conformation of the proline improved the arginase potency over the initial lead. The novel synthetic strategies reported here not only enable access to previously unknown stereochemically complex proline derivatives but also provide a foundation for the future synthesis of bicyclic proline analogs, which incorporate inherent three-dimensional character into building blocks, medicine, and catalysts and could have a profound impact on the conformation of proline-containing peptides and macrocycles.",

keywords = "Bicyclic proline, Arginase inhibitor, Conformation control",

author = "Derun Li and Hongjun Zhang and Lyons, {Thomas W.} and Min Lu and Abdelghani Achab and Qinglin Pu and Matthew Childers and Mitcheltree, {Matthew J.} and Jialiang Wang and Martinot, {Theodore A.} and McMinn, {Spencer E.} and Sloman, {David L.} and Anandan Palani and Adam Beard and Lisa Nogle and Symon Gathiaka and Josep Sauri and Hai-Young Kim and Donovon Adpressa and Peter Spacciapoli and Miller, {J. Richard} and Palte, {Rachel L.} and Lesburg, {Charles A.} and Jared Cumming and Christian Fischer",

year = "2021",

month = nov,

day = "11",

doi = "10.1021/acsmedchemlett.1c00258",

language = "English",

volume = "12",

pages = "1678--1688",

journal = "Acs Medicinal Chemistry Letters",

issn = "1948-5875",

publisher = "Amer Chemical Soc",

number = "11",

}

Li, D, Zhang, H, Lyons, TW, Lu, M, Achab, A, Pu, Q, Childers, M, Mitcheltree, MJ, Wang, J, Martinot, TA, McMinn, SE, Sloman, DL, Palani, A, Beard, A, Nogle, L, Gathiaka, S, Sauri, J, Kim, H-Y, Adpressa, D, Spacciapoli, P, Miller, JR, Palte, RL, Lesburg, CA, Cumming, J & Fischer, C 2021, 'Comprehensive Strategies to Bicyclic Prolines: Applications in the Synthesis of Potent Arginase Inhibitors', Acs Medicinal Chemistry Letters, vol. 12, núm. 11, pàg. 1678-1688. https://doi.org/10.1021/acsmedchemlett.1c00258

TY - JOUR

T1 - Comprehensive Strategies to Bicyclic Prolines

T2 - Applications in the Synthesis of Potent Arginase Inhibitors

AU - Li, Derun

AU - Zhang, Hongjun

AU - Lyons, Thomas W.

AU - Lu, Min

AU - Achab, Abdelghani

AU - Pu, Qinglin

AU - Childers, Matthew

AU - Mitcheltree, Matthew J.

AU - Wang, Jialiang

AU - Martinot, Theodore A.

AU - McMinn, Spencer E.

AU - Sloman, David L.

AU - Palani, Anandan

AU - Beard, Adam

AU - Nogle, Lisa

AU - Gathiaka, Symon

AU - Sauri, Josep

AU - Kim, Hai-Young

AU - Adpressa, Donovon

AU - Spacciapoli, Peter

AU - Miller, J. Richard

AU - Palte, Rachel L.

AU - Lesburg, Charles A.

AU - Cumming, Jared

AU - Fischer, Christian

PY - 2021/11/11

Y1 - 2021/11/11

N2 - Comprehensive synthetic strategies afforded a diverse set of structurally unique bicyclic proline-containing arginase inhibitors with a high degree of three-dimensionality. The analogs that favored the C gamma-exo conformation of the proline improved the arginase potency over the initial lead. The novel synthetic strategies reported here not only enable access to previously unknown stereochemically complex proline derivatives but also provide a foundation for the future synthesis of bicyclic proline analogs, which incorporate inherent three-dimensional character into building blocks, medicine, and catalysts and could have a profound impact on the conformation of proline-containing peptides and macrocycles.

AB - Comprehensive synthetic strategies afforded a diverse set of structurally unique bicyclic proline-containing arginase inhibitors with a high degree of three-dimensionality. The analogs that favored the C gamma-exo conformation of the proline improved the arginase potency over the initial lead. The novel synthetic strategies reported here not only enable access to previously unknown stereochemically complex proline derivatives but also provide a foundation for the future synthesis of bicyclic proline analogs, which incorporate inherent three-dimensional character into building blocks, medicine, and catalysts and could have a profound impact on the conformation of proline-containing peptides and macrocycles.

KW - Bicyclic proline

KW - Arginase inhibitor

KW - Conformation control

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DO - 10.1021/acsmedchemlett.1c00258

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SN - 1948-5875

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SP - 1678

EP - 1688

JO - Acs Medicinal Chemistry Letters

JF - Acs Medicinal Chemistry Letters

IS - 11

ER -

Comprehensive Strategies to Bicyclic Prolines: Applications in the Synthesis of Potent Arginase Inhibitors

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