Chemoselective Oxime Reactions in Proteins and Peptides by Using an Optimized Oxime Strategy: The Demise of Levulinic Acid

被引：13
|
作者：
Agten, Stijn M. [1 ]
Suylen, Dennis [1 ]
Ippel, Hans [1 ]
Kokozidou, Maria [1 ]
Tans, Guido [1 ]
van de Vijver, Pieter [1 ]
Koenen, Rory R. [1 ]
Hackeng, Tilman M. [1 ]
机构：
[1] Maastricht Univ, Dept Biochem, Cardiovasc Res Inst Maastricht CARIM, NL-6200 MD Maastricht, Netherlands
来源：
CHEMBIOCHEM | 2013年 / 14卷 / 18期
关键词：
bioconjugation; ketones; oximes; peptides; RANTES; CATALYSIS; LIGATION;
D O I：
10.1002/cbic.201300598
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Selecting the right partner faster: In protein chemoselective conjugation, the use of levulinic acid for ketone introduction leads to slow oxime formation and poor yield because of internal cyclization, especially at low concentrations. A mechanism for cyclization is proposed and alternative keto-acids have been tested. These showed faster formation of oximes without side products. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：2431 / 2434
页数：4
相关论文
共 50 条
  • [1] Efficient and Chemoselective Surface Immobilization of Proteins by Using Aniline-Catalyzed Oxime Chemistry
    Lempens, Edith H. M.
    Helms, Brett A.
    Merkx, Maarten
    Meijer, E. W.
    CHEMBIOCHEM, 2009, 10 (04) : 658 - 662
  • [2] Oxime and thiazolidine chemoselective ligation reactions: a green method for cotton functionalization
    Francesca Albini
    Barbara Biondi
    Luana Lastella
    Cristina Peggion
    Cellulose, 2023, 30 : 5573 - 5587
  • [3] Oxime and thiazolidine chemoselective ligation reactions: a green method for cotton functionalization
    Albini, Francesca
    Biondi, Barbara
    Lastella, Luana
    Peggion, Cristina
    CELLULOSE, 2023, 30 (09) : 5573 - 5587
  • [4] RESONANCE-ASSISTED HYDROGEN-BONDS BETWEEN OXIME AND CARBOXYL GROUP - COMPARISON OF TETRAMERIC STRUCTURES OF 4-METHYL-2-OXOPENTANOIC ACID OXIME AND LEVULINIC ACID OXIME
    MAURIN, JK
    LES, A
    WINNICKAMAURIN, M
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1995, 51 : 232 - 240
  • [5] STUDIES ON THE UTILIZATION OF LEVULINIC ACID .1. THE ANTIMICROBIAL ACTIVITIES OF LEVULINIC ACID OXIME AND SOME RELATED COMPOUNDS
    TAKAMIYA, K
    JOURNAL OF ANTIBIOTICS, 1956, 9 (06): : 218 - 224
  • [6] SYNTHESIS OF COVALENT RANTES-PF4 HETERODIMERS USING AN OPTIMIZED OXIME STRATEGY
    Agten, S.
    Suylen, D.
    Ippel, H.
    Mayo, K.
    Weber, C.
    Koenen, R.
    Hackeng, T.
    JOURNAL OF PEPTIDE SCIENCE, 2014, 20 : S85 - S86
  • [7] Preparation of large macrocyclic peptides using the oxime resin
    Blanchette, Jean-Philippe
    Ferland, Patrick
    Voyer, Normand
    TETRAHEDRON LETTERS, 2007, 48 (28) : 4929 - 4933
  • [8] Chemoselective pre-conjugate radiohalogenation of unprotected mono- and multimeric peptides via oxime formation
    Poethko, T
    Schottelius, M
    Thumshirn, G
    Herz, M
    Haubner, R
    Henriksen, G
    Kessler, H
    Schwaiger, M
    Wester, HJ
    RADIOCHIMICA ACTA, 2004, 92 (4-6) : 317 - 327
  • [9] Chemoselective Capture of Glycans for Analysis on Gold Nanoparticles: Carbohydrate Oxime Tautomers Provide Functional Recognition by Proteins
    Thygesen, Mikkel B.
    Sauer, Jorgen
    Jensen, Knud J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (07) : 1649 - 1660
  • [10] New strategy for the synthesis of 3′,5′-bifunctionalized oligonucleotide conjugates through sequential formation of chemoselective oxime bonds
    Edupuganti, OP
    Singh, Y
    Defrancq, E
    Dumy, P
    CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (23) : 5988 - 5995
12345