Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase

Hea Ok Kim; Su Jeong Yoo; Hee Sung Ahn; Won Jun Choi; Hyung Ryong Moon; Kang Man Lee; Moon Woo Chun; Lak Shin Jeong

doi:10.1016/j.bmcl.2004.02.039

Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase

Hea Ok Kim
, Su Jeong Yoo
, Hee Sung Ahn
, Won Jun Choi
, Hyung Ryong Moon
, Kang Man Lee
, Moon Woo Chun
, Lak Shin Jeong

Department of Pharmacy

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

26 Scopus citations

Abstract

Fluoro-DHCeA (4) was efficiently synthesized from D-cyclopentenone derivative 5 using electrophilic fluorination as a key step. Fluoro-DHCeA (4) was found to be as potent as DHCeA (3), but exhibited irreversible inhibition of enzyme unlike DHCeA (3) showing reversible inhibition. From this study, 4 ^′-hydroxymethyl groups of neplanocin A and fluoro-neplanocin A played an important role in binding to the active site of the enzyme.

Original language	English
Pages (from-to)	2091-2093
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	14
Issue number	9
DOIs	https://doi.org/10.1016/j.bmcl.2004.02.039
State	Published - 3 May 2004

Keywords

Antiviral
Carbocyclic nucleosides
Electrophilic fluorination
S-Adenosylhomocysteine hydrolase

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10.1016/j.bmcl.2004.02.039

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title = "Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase",

abstract = "Fluoro-DHCeA (4) was efficiently synthesized from D-cyclopentenone derivative 5 using electrophilic fluorination as a key step. Fluoro-DHCeA (4) was found to be as potent as DHCeA (3), but exhibited irreversible inhibition of enzyme unlike DHCeA (3) showing reversible inhibition. From this study, 4 ′-hydroxymethyl groups of neplanocin A and fluoro-neplanocin A played an important role in binding to the active site of the enzyme.",

keywords = "Antiviral, Carbocyclic nucleosides, Electrophilic fluorination, S-Adenosylhomocysteine hydrolase",

author = "Kim, \{Hea Ok\} and Yoo, \{Su Jeong\} and Ahn, \{Hee Sung\} and Choi, \{Won Jun\} and Moon, \{Hyung Ryong\} and Lee, \{Kang Man\} and Chun, \{Moon Woo\} and Jeong, \{Lak Shin\}",

year = "2004",

month = may,

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doi = "10.1016/j.bmcl.2004.02.039",

language = "English",

volume = "14",

pages = "2091--2093",

journal = "Bioorganic and Medicinal Chemistry Letters",

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publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase

AU - Kim, Hea Ok

AU - Yoo, Su Jeong

AU - Ahn, Hee Sung

AU - Choi, Won Jun

AU - Moon, Hyung Ryong

AU - Lee, Kang Man

AU - Chun, Moon Woo

AU - Jeong, Lak Shin

PY - 2004/5/3

Y1 - 2004/5/3

N2 - Fluoro-DHCeA (4) was efficiently synthesized from D-cyclopentenone derivative 5 using electrophilic fluorination as a key step. Fluoro-DHCeA (4) was found to be as potent as DHCeA (3), but exhibited irreversible inhibition of enzyme unlike DHCeA (3) showing reversible inhibition. From this study, 4 ′-hydroxymethyl groups of neplanocin A and fluoro-neplanocin A played an important role in binding to the active site of the enzyme.

AB - Fluoro-DHCeA (4) was efficiently synthesized from D-cyclopentenone derivative 5 using electrophilic fluorination as a key step. Fluoro-DHCeA (4) was found to be as potent as DHCeA (3), but exhibited irreversible inhibition of enzyme unlike DHCeA (3) showing reversible inhibition. From this study, 4 ′-hydroxymethyl groups of neplanocin A and fluoro-neplanocin A played an important role in binding to the active site of the enzyme.

KW - Antiviral

KW - Carbocyclic nucleosides

KW - Electrophilic fluorination

KW - S-Adenosylhomocysteine hydrolase

UR - https://www.scopus.com/pages/publications/1842690640

U2 - 10.1016/j.bmcl.2004.02.039

DO - 10.1016/j.bmcl.2004.02.039

M3 - Article

C2 - 15080985

AN - SCOPUS:1842690640

SN - 0960-894X

VL - 14

SP - 2091

EP - 2093

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 9

ER -

Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase

Abstract

Keywords

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