Remarkable and Unexpected Mechanism for (S)-3-Amino-4-(difluoromethylenyl)cyclohex-1-ene-1-carboxylic Acid as a Selective Inactivator of Human Ornithine Aminotransferase

被引:0
|
作者
Zhu, Wei [1 ]
Doubleday, Peter F. [2 ]
Butrin, Arseniy [3 ]
Weerawarna, Pathum M. [1 ]
Melani, Rafael D. [2 ]
Catlin, Daniel S. [3 ]
Dwight, Timothy A. [1 ]
Liu, Dali [3 ]
Kelleher, Neil L. [1 ,2 ]
Silverman, Richard B. [1 ,2 ,4 ]
机构
[1] Department of Chemistry, Chemistry of Life Processes Institute, Center for Molecular Innovation and Drug Discovery, Center for Developmental Therapeutics, Northwestern University, Evanston,IL,60208, United States
[2] Department of Molecular Biosciences, Northwestern University, Evanston,IL,60208, United States
[3] Department of Chemistry and Biochemistry, Loyola University Chicago, Chicago,IL,60660, United States
[4] Department of Pharmacology, Northwestern University, Chicago,IL,60611, United States
来源
Journal of the American Chemical Society | 2021年 / 143卷 / 21期
关键词
Enzymes;
D O I
暂无
中图分类号
学科分类号
摘要
引用
收藏
页码:8193 / 8207
相关论文
共 50 条
  • [21] Accumulation and transport mechanism of anti-1-amino-3-[18F]fluorocyclobutane-1-carboxylic acid in representative human carcinomas
    Kobayashi, Masato
    Kagawa, Shinya
    Nishii, Ryuichi
    Takahashi, Fumiya
    Ohe, Kazuyo
    Yoshimoto, Mitsuyoshi
    Shikano, Naoto
    Higashi, Tatsuya
    Nagamachi, Shigeki
    Kawai, Keiichi
    JOURNAL OF NUCLEAR MEDICINE, 2010, 51
  • [22] Chemoenzymatic Sequential Multistep One-Pot Reaction for the Synthesis of (1S,2R)-1-(Methoxycarbonyl)cyclohex-4-ene-2-carboxylic Acid with Recombinant Pig Liver Esterase
    Suess, Philipp
    Borchert, Sonja
    Hinze, Janine
    Iller, Sabine
    von Langermann, Jan
    Kragl, Udo
    Bornscheuer, Uwe T.
    Wardenga, Rainer
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (12) : 2034 - 2038
  • [23] Structural modifications of (1S,3S)-3-amino-4-difluoromethylene-cyclopentanecarboxylic acid, a potent irreversible inhibitor of GABA aminotransferase
    Yuan, Hai
    Silverman, Richard B.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (06) : 1651 - 1654
  • [24] ACID-CATALYZED REARRANGEMENT OF 4-ALLYL-CYCLOHEX-2-ENE-1-OLENE - EXAMPLES FOR CHARGE CONTROLLED [3S,4S]-REARRANGEMENT OF CYCLIC ALLYL CATIONS
    VITTORELLI, P
    PETERKATALINIC, J
    MUKHERJEEMULLER, G
    HANSEN, HJ
    SCHMID, H
    HELVETICA CHIMICA ACTA, 1975, 58 (05) : 1379 - 1425
  • [25] SYNTHESES OF 2-[(1S,3S)-1-AMINO-3-CARBOXY-3-HYDROXYPROPYL]-THIAZOLE-4-CARBOXYLIC ACID AND THE TRIPEPTIDE SKELETON OF NOSIHEPTIDE CONTAINING THE ACID
    SHIN, CG
    NAKAMURA, Y
    YAMADA, Y
    YONEZAWA, Y
    UMEMURA, K
    YOSHIMURA, J
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (11) : 3151 - 3160
  • [26] An unexpected acid mediated rearrangement of monoethylene ketal of 2-methyl-2-(3-methylbut-2-en-l-y1)cyclohex-4-ene-1,3-diones to chromane
    Sreenivas, Kukkamudi
    Khan, Faiz Ahmed
    TETRAHEDRON LETTERS, 2018, 59 (13) : 1244 - 1248
  • [27] 1-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid as a Tic mimetic: Application in the synthesis of potent human melanocortin-4 receptor selective agonists
    Bakshi, RK
    Hong, QM
    Olson, JT
    Ye, ZX
    Sebhat, IK
    Weinberg, DH
    MacNeil, T
    Kalyani, RN
    Tang, R
    Martin, WJ
    Strack, A
    McGowan, E
    Tamvakopoulos, C
    Miller, RR
    Stearns, RA
    Tang, W
    Maclntyre, DE
    van der Ploeg, LHT
    Patchett, AA
    Nargund, RP
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (14) : 3430 - 3433
  • [28] (2S, 3S)-3-Amino-4-(3,3-difluoropyrrolidin-1-yl)-N,N-dimethyl4-oxo-2-(4-[1,2,4]triazolo[1,5-a]pyridin-6-ylphenyl)butanamide:: A selective α-amino amide dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes
    Edmondson, Scott D.
    Mastracchio, Anthony
    Mathvink, Robert J.
    He, Jiafang
    Harper, Bart
    Park, You-Jung
    Beconi, Maria
    Di Salvo, Jerry
    Eiermann, George J.
    He, Huaibing
    Leiting, Barbara
    Leone, Joseph F.
    Levorse, Dorothy A.
    Lyons, Kathryn
    Patel, Reshma A.
    Patel, Sangita B.
    Petrov, Aleksandr
    Scapin, Giovanna
    Shang, Jackie
    Roy, Ranabir Sinha
    Smith, Aaron
    Wu, Joseph K.
    Xu, Shiyao
    Zhu, Bing
    Thornberry, Nancy A.
    Weber, Ann E.
    JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (12) : 3614 - 3627
  • [29] Imidazoacridinone antitumor agent C-1311 as a selective mechanism-based inactivator of human cytochrome P450 1A2 and 3A4 isoenzymes
    Agnieszka Potęga
    Barbara Fedejko-Kap
    Zofia Mazerska
    Pharmacological Reports, 2016, 68 : 663 - 670
  • [30] (±)-( 1S, 2R, 5S)-5-amino-2-fluorocyclohex-3-enecarboxylic acid.: A potent GABA aminotransferase inactivator that irreversibly inhibits via an elimination-aromatization pathway
    Wang, Zhiyong
    Yuan, Hai
    Nikolic, Dejan
    Van Breemen, Richard B.
    Silverman, Richard B.
    BIOCHEMISTRY, 2006, 45 (48) : 14513 - 14522