Functionalization of cysteine derivatives by unsymmetrical disulfide bond formation

被引：35

作者：

Szymelfejnik, Mateusz ^{[1
]}

Demkowicz, Sebastian ^{[1
]}

Rachon, Janusz ^{[1
]}

Witt, Dariusz ^{[1
]}

机构：

[1] Gdansk Technol Univ, Fac Chem, Dept Organ Chem, PL-80952 Gdansk, Poland

来源：

SYNTHESIS-STUTTGART | 2007年 / 22期

关键词：

unsymmetrical disulfides; L-cystine; L-cysteine; sulfenyl bromide; thiols;

D O I：

10.1055/s-2007-990853

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a convenient method for the synthesis of unsymmetrical disulfides of L-cysteine under mild conditions in good to excellent yields. The described method is based on the straightforward preparation of 5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinane-2-sulfenyl bromide from readily available bis(5,5dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide. The unsymmetrical disulfides can be obtained for L-cysteine derivatives and thiols bearing neutral, basic, or acidic functionalities.

引用

页码：3528 / 3534

页数：7

共 50 条

[1] The organophosphorus sulfenyl bromides as versatile reagents for cysteine derivatives functionalization by unsymmetrical disulfide bond formation
Szymelfejnik, Mateusz
Demkowicz, Sebastian
Witt, Dariusz
Rachon, Janusz
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (2-3) : 415 - 419
[2] PREPARATION OF BOC-[S-(3-NITRO-2-PYRIDINESULFENYL)]-CYSTEINE AND ITS USE FOR UNSYMMETRICAL DISULFIDE BOND FORMATION
BERNATOWICZ, MS
MATSUEDA, R
MATSUEDA, GR
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1986, 28 (02): : 107 - 112
[3] Disulfide Bond Formation and Cysteine Exclusion in Gram-positive Bacteria
Daniels, Robert
Mellroth, Peter
Bernsel, Andreas
Neiers, Fabrice
Normark, Staffan
von Heijne, Gunnar
Henriques-Normark, Birgitta
JOURNAL OF BIOLOGICAL CHEMISTRY, 2010, 285 (05) : 3300 - 3309
[4] Secretion of cysteine and glutathione in response to protein disulfide bond formation in the ER
Carelli, S
Cabibbo, A
Ceriotti, A
Fassina, G
Rubartelli, A
Sitia, R
MOLECULAR BIOLOGY OF THE CELL, 1997, 8 : 564 - 564
[5] Aryloxymaleimides for cysteine modification, disulfide bridging and the dual functionalization of disulfide bonds
Marculescu, Cristina
Kossen, Hanno
Morgan, Rachel E.
Mayer, Patrick
Fletcher, Sally A.
Tolner, Berend
Chester, Kerry A.
Jones, Lyn H.
Baker, James R.
CHEMICAL COMMUNICATIONS, 2014, 50 (54) : 7139 - 7142
[6] Cysteine sulfenic Acid as an Intermediate in Disulfide Bond Formation and Nonenzymatic Protein Folding
Rehder, Douglas S.
Borges, Chad R.
BIOCHEMISTRY, 2010, 49 (35) : 7748 - 7755
[7] Effects of disulfide bond and cholesterol derivatives on human calcitonin amyloid formation
Lantz, Richard
Busbee, Brian
Wojcikiewicz, Ewa P.
Du, Deguo
BIOPOLYMERS, 2020, 111 (05)
[8] Identification of the alternative oxidase cysteine residue involved in regulatory disulfide bond formation.
Rhoads, DM
Umbach, AL
Siedow, JN
PLANT PHYSIOLOGY, 1997, 114 (03) : 1016 - 1016
[9] A new cysteine in rotavirus VP4 participates in the formation of an alternate disulfide bond
Cuadras, MA
Méndez, E
Aries, CF
López, S
JOURNAL OF GENERAL VIROLOGY, 1998, 79 : 2673 - 2677
[10] Effect of cysteine mutagenesis on the function and disulfide bond formation of human ABCG2
Liu, Yang
Yang, Youyun
Qi, Jing
Peng, Hui
Zhang, Jian-Ting
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2008, 326 (01): : 33 - 40

← 1 2 3 4 5 →