Nucleophilic catalysis of oxime ligation

被引：392

作者：

Dirksen, Anouk

Hackeng, Tilman M.

Dawson, Philip E.

机构：

[1] Scripps Res Inst, Skaggs Inst Chem Biol, Dept Cell Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, Dept Chem, La Jolla, CA 92037 USA

[3] Univ Maastricht, Cardiovasc Res Inst Maastricht, NL-6200 MD Maastricht, Netherlands

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 45期

关键词：

bioconjugation; nucleophilic catalysis; peptides; Schiff bases; transimination;

D O I：

10.1002/anie.200602877

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Aniline acts as a nucleophilic catalyst of oxime ligation in aqueous solution through formation of the orange-colored intermediate. The method is demonstrated by acceleration of the oxime ligation of peptides at pH 4.5 and pH 7, which extends the scope of this reaction to conditions relevant for the bioconjugation of macromolecules (see scheme). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7581 / 7584

页数：4

共 26 条

[1] WEAK BASES IN STRONG ACIDS .4. BASICITY SCALE FOR CARBONYL COMPOUNDS BASED ON HEATS OF IONIZATION IN FLUOROSULFURIC ACID
ARNETT, EM
QUIRK, RP
LARSEN, JW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (13) : 3977 - &
[2] THE PHYSICAL AND CHEMICAL PROPERTIES OF THE METHYLHYDROXYLAMINES
BISSOT, TC
PARRY, RW
CAMPBELL, DH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (04) : 796 - 800
[3] Chemical synthesis of proteins
Borgia, JA
Fields, GB
[J]. TRENDS IN BIOTECHNOLOGY, 2000, 18 (06) : 243 - 251
[4] TOTAL CHEMICAL SYNTHESIS OF A UNIQUE TRANSCRIPTION FACTOR-RELATED PROTEIN - CMYC-MAX
CANNE, LE
FERREDAMARE, AR
BURLEY, SK
KENT, SBH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) : 2998 - 3007
[5] CAREY FA, 1990, ADV ORG CHEM, P447
[6] Site-specific labeling of cell surface proteins with biophysical probes using biotin ligase
Chen, I
Howarth, M
Lin, WY
Ting, AY
[J]. NATURE METHODS, 2005, 2 (02) : 99 - 104
[7] NUCLEOPHILIC CATALYSIS OF SEMICARBAZONE FORMATION BY ANILINES
CORDES, EH
JENCKS, WP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) : 826 - &
[8] ON MECHANISM OF SCHIFF BASE FORMATION AND HYDROLYSIS
CORDES, EH
JENCKS, WP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) : 832 - &
[9] Synthesis of native proteins by chemical ligation
Dawson, PE
Kent, SBH
[J]. ANNUAL REVIEW OF BIOCHEMISTRY, 2000, 69 : 923 - 960
[10] CONSTRUCTION OF PROTEIN ANALOGS BY SITE-SPECIFIC CONDENSATION OF UNPROTECTED FRAGMENTS
GAERTNER, HF
ROSE, K
COTTON, R
TIMMS, D
CAMBLE, R
OFFORD, RE
[J]. BIOCONJUGATE CHEMISTRY, 1992, 3 (03) : 262 - 268

← 1 2 3 →