RhCl3-CATALYZED DISULFIDE EXCHANGE REACTION OF INSULIN AND DITHIODIGLYCOLIC ACID

被引：10

作者：

Arisawa, Mieko ^{[1
]}

Kuwajima, Manabu ^{[1
]}

Suwa, Atsushi ^{[1
]}

Yamaguchi, Masahiko ^{[2
]}

机构：

[1] Tohoku Univ, Dept Organ Chem, Grad Sch Pharmaceut Sci, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Adv Inst Mat Res, WPI Res Ctr, Sendai, Miyagi 9808577, Japan

来源：

HETEROCYCLES | 2010年 / 80卷 / 02期

关键词：

Rhodium Chloride; Disulfide Exchange Reaction; Catalysis; A7/B7; Disulfide; Insulin; OXIDATIVE CROSS-LINKING; RHODIUM CARBENOIDS; ALKYLATION; COMPLEXES;

D O I：

10.3987/COM-09-S(S)110

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

RhCl3 catalyzed the alkylthio exchange reaction of insulin and dithiodiglycolic acid in water under homogeneous conditions. Insulin was rapidly consumed, and mono- and bis-exchanged insulin were formed along with the disulfide exchanged A and B chain. The disulfide bond at the A7/B7 was initially exchanged, which was followed by the A6/A11 and A20/B19 disulfides.

引用

收藏

页码：1239 / 1248

页数：10

相关论文

共 11 条

[1] Selective tryptophan modification with rhodium carbenoids in aqueous solution [J].

Antos, JM ;

Francis, MB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10256-10257

[2] Chemoselective Tryptophan Labeling with Rhodium Carbenoids at Mild pH [J].

Antos, John M. ;

McFarland, Jesse M. ;

Iavarone, Anthony T. ;

Francis, Matthew B. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) :6301-6308

[3] RhCl3-catalyzed disulfide exchange reaction using water solvent in homogeneous and heterogeneous systems [J].

Arisawa, M ;

Suwa, A ;

Yamaguchi, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (06) :1159-1168

[4] HIGHLY SPECIFIC OXIDATIVE CROSS-LINKING OF PROTEINS MEDIATED BY A NICKEL-PEPTIDE COMPLEX [J].

BROWN, KC ;

YANG, SH ;

KODADEK, T .

BIOCHEMISTRY, 1995, 34 (14) :4733-4739

[5] PREPARATION AND PROPERTIES OF MIXED DISULFIDES OF BOVINE INSULIN WITH GLUTATHIONE AND THIOGLYCOLLIC ACID [J].

BUSSE, WD ;

GATTNER, HG .

HOPPE-SEYLERS ZEITSCHRIFT FUR PHYSIOLOGISCHE CHEMIE, 1973, 354 (09) :1057-1067

[6] Techniques: Oxidative cross-linking as an emergent tool for the analysis of receptor-mediated signalling events [J].

Kodadek, T ;

Duroux-Richard, I ;

Bonnafous, JC .

TRENDS IN PHARMACOLOGICAL SCIENCES, 2005, 26 (04) :210-217

[7] Allyl sulfides are privileged substrates in aqueous cross-metathesis: Application to site-selective protein modification [J].

Lin, Yuya A. ;

Chalker, Justin M. ;

Floyd, Nicola ;

Bernardes, Goncalo J. L. ;

Davis, Benjamin G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (30) :9642-+

[8] Pd(II) complexes mediated hydrolytic cleavage of insulin B chain: Regioselectivity and influence of peptide secondary structure [J].

Luo, XM ;

He, WJ ;

Zhang, Y ;

Guo, ZJ ;

Zhu, LG .

CHEMISTRY LETTERS, 2000, (09) :1030-1031

[9] Reductive alkylation of proteins using iridium catalyzed transfer hydrogenation [J].

McFarland, JM ;

Francis, MB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) :13490-13491

[10] DISULPHIDE INTERCHANGE REACTIONS [J].

RYLE, AP ;

SANGER, F .

BIOCHEMICAL JOURNAL, 1955, 60 (1-4) :535-540