Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase

Lak Shin Jeong; Su Jeong Yoo; Kang Man Lee; Mi Jeong Koo; Won Jun Choi; Hea Ok Kim; Hyung Ryong Moon; Min Young Lee; Jae Gyu Park; Sang Kook Lee; Moon Woo Chun

doi:10.1021/jm025557z

Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase

Lak Shin Jeong, Su Jeong Yoo, Kang Man Lee, Mi Jeong Koo, Won Jun Choi, Hea Ok Kim, Hyung Ryong Moon, Min Young Lee, Jae Gyu Park, Sang Kook Lee, Moon Woo Chun

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

70 Scopus citations

Abstract

Fluoroneplanocin A (12) was designed as a novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase (SAH) and efficiently synthesized via an electrophilic vinyl fluorination reaction (n-BuLi, N-fluorobenzenesulfonimide at -78 °C). Fluoroneplanocin A exhibited 2-fold more potent SAH inhibitory activity than the parent neplanocin A. A new mechanism of irreversible inhibition discovered in this work might provide new alternatives in the design of a different class of antiviral agents operating via SAH inhibition.

Original language	English
Pages (from-to)	201-203
Number of pages	3
Journal	Journal of Medicinal Chemistry
Volume	46
Issue number	2
DOIs	https://doi.org/10.1021/jm025557z
State	Published - 16 Jan 2003

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Jeong, L. S., Yoo, S. J., Lee, K. M., Koo, M. J., Choi, W. J., Kim, H. O., Moon, H. R., Lee, M. Y., Park, J. G., Lee, S. K., & Chun, M. W. (2003). Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase. Journal of Medicinal Chemistry, 46(2), 201-203. https://doi.org/10.1021/jm025557z

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abstract = "Fluoroneplanocin A (12) was designed as a novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase (SAH) and efficiently synthesized via an electrophilic vinyl fluorination reaction (n-BuLi, N-fluorobenzenesulfonimide at -78 °C). Fluoroneplanocin A exhibited 2-fold more potent SAH inhibitory activity than the parent neplanocin A. A new mechanism of irreversible inhibition discovered in this work might provide new alternatives in the design of a different class of antiviral agents operating via SAH inhibition.",

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doi = "10.1021/jm025557z",

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AU - Jeong, Lak Shin

AU - Yoo, Su Jeong

AU - Lee, Kang Man

AU - Koo, Mi Jeong

AU - Choi, Won Jun

AU - Kim, Hea Ok

AU - Moon, Hyung Ryong

AU - Lee, Min Young

AU - Park, Jae Gyu

AU - Lee, Sang Kook

AU - Chun, Moon Woo

PY - 2003/1/16

Y1 - 2003/1/16

N2 - Fluoroneplanocin A (12) was designed as a novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase (SAH) and efficiently synthesized via an electrophilic vinyl fluorination reaction (n-BuLi, N-fluorobenzenesulfonimide at -78 °C). Fluoroneplanocin A exhibited 2-fold more potent SAH inhibitory activity than the parent neplanocin A. A new mechanism of irreversible inhibition discovered in this work might provide new alternatives in the design of a different class of antiviral agents operating via SAH inhibition.

AB - Fluoroneplanocin A (12) was designed as a novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase (SAH) and efficiently synthesized via an electrophilic vinyl fluorination reaction (n-BuLi, N-fluorobenzenesulfonimide at -78 °C). Fluoroneplanocin A exhibited 2-fold more potent SAH inhibitory activity than the parent neplanocin A. A new mechanism of irreversible inhibition discovered in this work might provide new alternatives in the design of a different class of antiviral agents operating via SAH inhibition.

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JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 2

ER -

Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase

Abstract

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