Selective Derivatization of N-Terminal Cysteines Using Cyclopentenediones

被引：10

作者：

Brun, Omar ^{[1
]}

Agramunt, Jordi ^{[1
]}

Raich, Lluis ^{[1
,2
]}

Rovira, Carme ^{[1
,2
,4
]}

Pedroso, Enrique ^{[1
,3
]}

Grandas, Anna ^{[1
,3
]}

机构：

[1] Univ Barcelona, Fac Quim, Dept Quim Inorgan & Organ, Marti & Franques 1-11, E-08028 Barcelona, Spain

[2] Univ Barcelona, Fac Quim, IQTCUB, Seccio Q Organ, Marti & Franques 1-11, E-08028 Barcelona, Spain

[3] Univ Barcelona, Fac Quim, IBUB, Seccio Q Organ, Marti & Franques 1-11, E-08028 Barcelona, Spain

[4] ICREA, Passeig Lluis Co 23, Barcelona 08010, Spain

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 19期

关键词：

SITE-SPECIFIC CONJUGATION; FLUORESCENT-PROBE; HOMOCYSTEINE; PROTEINS; OLIGONUCLEOTIDES; GLUTATHIONE; STABILITY; PEPTIDES; REAGENTS; BIOCONJUGATION;

D O I：

10.1021/acs.orglett.6b02301

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The outcome of the Michael-type reaction between thiols and 2,2-disubstituted cyclopentenediones varies depending on the thiol. Stable compounds with two fused rings were formed upon reaction with 1,2-aminothiols (such as N-terminal cysteines in peptides). Other thiols gave reversibly Michael-type adducts that were in equilibrium with the starting materials. This differential reactivity allows differently placed cysteines to be distinguished and has been exploited to prepare bioconjugates incorporating two or three different moieties.

引用

页码：4836 / 4839

页数：4

共 50 条

[41] Selective fluorescence detection of cysteine and N-terminal cysteine peptide residues
Lim, Soojin
Escobedo, Jorge O.
Lowry, Mark
Xu, Xiangyang
Strongin, Robert
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (31) : 5707 - 5709
[42] Engineering ClpS for selective and enhanced N-terminal amino acid binding
Jennifer Tullman
Nicholas Callahan
Benjamin Ellington
Zvi Kelman
John P. Marino
[J]. Applied Microbiology and Biotechnology, 2019, 103 : 2621 - 2633
[43] Characterization of the N-Terminal Heterogeneities of Monoclonal Antibodies Using In-Gel Charge Derivatization of α-Amines and LC-MS/MS
Ayoub, Daniel
Bertaccini, Diego
Diemer, Helene
Wagner-Rousset, Elsa
Colas, Olivier
Cianferani, Sarah
Van Dorsselaer, Alain
Beck, Alain
Schaeffer-Reiss, Christine
[J]. ANALYTICAL CHEMISTRY, 2015, 87 (07) : 3784 - 3790
[44] N-terminal labeling of proteins using initiator tRNA
Olejnik, J
Gite, S
Mamaev, S
Rothschild, KJ
[J]. METHODS, 2005, 36 (03) : 252 - 260
[45] N-terminal α-amino group modification of antibodies using a site-selective click chemistry method
Li, De-zhi
Han, Bing-nan
Wei, Rui
Yao, Gui-Yang
Chen, Zhizhen
Liu, Jie
Poon, Terence C. W.
Su, Wu
Zhu, Zhongyu
Dimitrov, Dimiter S.
Zhao, Qi
[J]. MABS, 2018, 10 (05) : 712 - 719
[46] Quantification of peptides using N-terminal isotope coding and C-terminal derivatization for sensitive analysis by micro liquid chromatography-tandem mass spectrometry
Sakaguchi, Yohei
Kinumi, Tomoya
Takatsu, Akiko
[J]. JOURNAL OF MASS SPECTROMETRY, 2016, 51 (12): : 1111 - 1119
[47] MASS-SPECTROMETRIC DETERMINATION OF N-TERMINAL TRYPTOPHAN AND N-TERMINAL HISTIDINE IN PEPTIDES
JAYASIMHULU, K
DAY, RA
[J]. BIOMEDICAL MASS SPECTROMETRY, 1980, 7 (08): : 321 - 326
[48] Role of N-terminal cysteines of Env7 in its palmitoylation, vacuolar localization, and fusion/fission regulation in cells
Manandhar, S. P.
Calle, E.
Gharakhanian, E.
[J]. MOLECULAR BIOLOGY OF THE CELL, 2013, 24
[49] An efficient site-selective, dual bioconjugation approach exploiting N-terminal cysteines as minimalistic handles to engineer tailored anti-HER2 affibody conjugates
Novak, Ana
Kersaudy, Florian
Berger, Sylvie
Morisset-Lopez, Severine
Lefoulon, Francois
Pifferi, Carlo
Aucagne, Vincent
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2023, 260
[50] Protein N-terminal Acetylation by the NatA Complex Is Critical for Selective Mitochondrial Degradation
Eiyama, Akinori
Okamoto, Koji
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2015, 290 (41) : 25034 - 25044

← 1 2 3 4 5 →