Highly Stable Meldrum's Acid Derivatives for Irreversible Aqueous Covalent Modification of Amines

被引：11
|
作者：
Davis, Garrett J. [1 ]
Sofka, Holly A. [1 ]
Jewett, John C. [1 ]
机构：
[1] Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 07期
关键词：
D O I：
10.1021/acs.orglett.0c00597
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This work describes the development of a highly stable and pH-responsive probe for lysine modification. The scaffold has marked stability in the presence of several biological nucleophiles and across a wide pH range (2-12). Several functional analogs showed robust labeling of a protein at pH > 9. Taken together, our system displays versatility and can be easily adapted for variety of applications, while demonstrating stability suitable for a wide range of biologically compatible systems.
引用
收藏
页码：2626 / 2629
页数：4
相关论文
共 50 条
  • [1] Enyne Meldrum′s acid derivatives: synthesis and Michael reactions with amines and thiols
    Sokov, S. A.
    Odin, I. S.
    Gusev, D. M.
    Kunavin, Yu A.
    Vologzhanina, A. V.
    Voronova, E. D.
    Golovanov, A. A.
    RUSSIAN CHEMICAL BULLETIN, 2020, 69 (02) : 305 - 312
  • [2] Enyne Meldrum´s acid derivatives: synthesis and Michael reactions with amines and thiols
    S. A. Sokov
    I. S. Odin
    D. M. Gusev
    Yu. A. Kunavin
    A. V. Vologzhanina
    E. D. Voronova
    A. A. Golovanov
    Russian Chemical Bulletin, 2020, 69 : 305 - 312
  • [3] Reactions of α-isobutyl-α-(methylthio)methylene Meldrum's acid with primary amines in aqueous DMSO
    Biswas, Supriya
    Ali, Mahammad
    Rappoport, Zvi
    Salim, Hatim
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2006, 84 (12): : 1679 - 1685
  • [4] Two methylsulfanylmethylene derivatives of Meldrum's acid
    Gould, RO
    Harris, SG
    McNab, H
    Parsons, S
    Withell, K
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1998, 54 : 234 - 236
  • [5] Two methylsulfanylmethylene derivatives of Meldrum's acid
    Gould, R.O.
    Harris, S.G.
    McNab, H.
    Parsons, S.
    Withell, K.
    Acta Crystallographica, Section C: Crystal Structure Communications, 1998, 54 (pt 2): : 234 - 236
  • [6] Irreversible covalent modification of type I dehydroquinase with a stable Schiff base
    Tizon, Lorena
    Maneiro, Maria
    Peon, Antonio
    Otero, Jose M.
    Lence, Emilio
    Poza, Sergio
    van Raaij, Mark J.
    Thompson, Paul
    Hawkins, Alastair R.
    Gonzalez-Bello, Concepcion
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (03) : 706 - 716
  • [7] Bentonite Catalyzed an Efficient and Green Synthesis of Arylidene Meldrum's Acid Derivatives in Aqueous Media
    Yahyazadehfar, Mahdieh
    Ahmadi, Sayed Ali
    Sheikhhosseini, Enayatollah
    Ghazanfari, Dadkhoda
    LETTERS IN ORGANIC CHEMISTRY, 2021, 18 (07) : 513 - 519
  • [8] Synthetic applications of the pyrolysis of Meldrum's acid derivatives
    Gaber, AAM
    McNab, H
    SYNTHESIS-STUTTGART, 2001, (14): : 2059 - 2074
  • [9] Synthetic applications of the pyrolysis of Meldrum's acid derivatives
    Gaber, A.E.-A.M.
    McNab, H.
    Synthesis, 2001, (14) : 2059 - 2074
  • [10] Radical Cyclization Cascades of Unsaturated Meldrum's Acid Derivatives
    Sautier, Brice
    Lyons, Sarah E.
    Webb, Michael R.
    Procter, David J.
    ORGANIC LETTERS, 2012, 14 (01) : 146 - 149
12345