2127-03-9 Usage
Description
2,2'-Dithiodipyridine, also known as Aldrithiol-2 or DPS, is a white to yellowish crystalline powder with chemical properties that make it a versatile reagent in various applications. It is a nucleocapsid zinc finger targeting compound that can abrogate the infectivity of human immunodeficiency virus type-1 virions. Its structure allows it to interact with different functional groups, making it a promising candidate for various uses.
Uses
Used in Chemical Synthesis:
2,2'-Dithiodipyridine is used as a reagent for the preparation of thiols and the activation or protection of carboxylic acids with triphenylphosphine. It facilitates the formation of desired products in chemical reactions and enhances the efficiency of the synthesis process.
Used in Analytical Chemistry:
2,2'-Dithiodipyridine is used as a reagent for the determination of sulfhydryl groups, preparation of amino acid active esters, and the thio esters of phosphoric acid. Its ability to react with specific functional groups makes it a valuable tool in the analysis and identification of various compounds.
Used in Peptide Synthesis:
As a peptide coupling reagent, 2,2'-Dithiodipyridine aids in the formation of peptide bonds between amino acid residues. It is particularly useful in the synthesis of complex peptides and proteins, contributing to the development of new pharmaceuticals and bioactive molecules.
Used in Oxidation Reactions:
2,2'-Dithiodipyridine acts as an oxidizing agent, enabling the conversion of specific functional groups to their oxidized forms. This property is useful in various chemical transformations and can be applied in the synthesis of a wide range of compounds.
Used in Glycoside Activation:
2,2'-Dithiodipyridine is used for the activation of glycosides, which are important intermediates in the synthesis of oligosaccharides and other carbohydrate-derived compounds. Its ability to activate glycosides facilitates the formation of glycosidic bonds, which are crucial for the biological activity of many molecules.
Used in Aldrithiol-2 Synthesis:
Aldrithiol-2, a derivative of 2,2'-Dithiodipyridine, is used in the synthesis of adenosine-5′-phosphoimidazolide. It is employed with PPh3 as a condensing agent in the amidation of carboxylic acid enantiomers for high-performance liquid chromatography (HPLC) separation. This application highlights the versatility of 2,2'-Dithiodipyridine and its derivatives in chemical synthesis and analysis.
Biochem/physiol Actions
2,2′-Dithiodipyridine mediates inter-unit disulfide cross-linking. It interacts with carbon nucleophiles to yield thiopyridyl derivatives.
Purification Methods
Recrystallise the disulfide H2O from *C6H6/pet ether (6:7), ligroin or *C6H6. The picrate has m 119o (from EtOH). [Walter et al. Justus Liebigs Ann Chem 695 7785 1966, Marckwald et al. Chem Ber 33 1556 1900, Brocklehurst & Little Biochem J 133 67,78 1973, Beilstein 21 III/IV 48.] It has been used as a 1mM solution in EtOH for the spectrophotometric estimation of thiols. Essentially the thiol displaces half the disulfide molecule liberating the 2-mercaptopyridine anion, thereby shifting the from 340nm (of the disulfide) to 268nm (of the anion) at pH 9, or 278nm in H2O. (Compare
Check Digit Verification of cas no
The CAS Registry Mumber 2127-03-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,2 and 7 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2127-03:
(6*2)+(5*1)+(4*2)+(3*7)+(2*0)+(1*3)=49
49 % 10 = 9
So 2127-03-9 is a valid CAS Registry Number.
2127-03-9Relevant articles and documents
Thione-thiol tautomerism and stability of 2- and 4-mercaptopyridines and 2-mercaptopyrimidines
Stoyanov,Petkov,Antonov,Stoyanova,Karagiannidis,Aslanidis
, p. 1482 - 1489 (1990)
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Visible-light-induced synthesis of benzothiophenes and benzoselenophenes via the annulation of thiophenols or 1,2-diphenyldiselane with alkynes
Xia, Xiao-Feng,Zhang, Guo-Wei,Zhu, Su-Li
, p. 2727 - 2730 (2017)
An effective metal-free photoredox-mediated tandem addition/cyclization reaction of thiophenols or 1,2-diphenyldiselane with alkynes leads to 2,3-disubstituted benzothiophenes and benzoselenophenes. Blue light irradiation of the organic dye, Mes-Acr-Mesu
Urea- Hydrogen Peroxide (UHP) oxidation of thiols to the corresponding disulfides promoted by maleic anhydride as mediator
Karami, Bahador,Montazerozohori,Habibi
, p. 1358 - 1363 (2005)
Urea-hydrogen peroxide (UHP) was used in the presence of maleic anhydride as mediator in a simple and convenient method for the oxidation in high yield of some thiols to the corresponding disulfides. Peroxymaleic acid formed in situ from the reaction of U
Synthesis of pyridothietone by flash vacuum pyrolysis of 2-mercaptonicotinic acid
Chou, Chin-Hsing,Chiu, Shao-Jung,Liu, Wei-Min
, p. 5285 - 5286 (2002)
The temperature dependence of products formed from flash vacuum pyrolysis (FVP) of 2-mercaptonicotinic acid 4 has been studied. FVP of 4 at 550°C and ca. 1×10-2 torr gave pyridothietone 3b and a trimer 5 as the major products. At higher temperature (800°C), FVP of 4 gave 2-mercaptopyridine 6 as the major product and 2,2′-dipyridyl disulphide 7 as the minor one.
Copper based on diaminonaphthalene-coated magnetic nanoparticles as robust catalysts for catalytic oxidation reactions and C-S cross-coupling reactions
Yarmohammadi, Nasrin,Ghadermazi, Mohammad,Mozafari, Roya
, p. 9366 - 9380 (2021/03/16)
In this work, the immobilization of copper(ii) on the surface of 1,8-diaminonaphthalene (DAN)-coated magnetic nanoparticles provides a highly active catalyst for the oxidation reaction of sulfides to sulfoxides and the oxidative coupling of thiols to disulfides using hydrogen peroxide (H2O2). This catalyst was also applied for the one-pot synthesis of symmetrical sulfidesviathe reaction of aryl halides with thiourea as the sulfur source in the presence of NaOH instead of former strongly basic and harsh reaction conditions. Under optimum conditions, the synthesis yields of sulfoxides, symmetrical sulfides, and disulfides were about 99%, 95%, and 96% respectively with highest selectivity. The heterogeneous copper-based catalyst has advantages such as the easy recyclability of the catalyst, the easy separation of the product and the less wastage of products during the separation of the catalyst. This heterogeneous nanocatalyst was characterized by FESEM, FT-IR, VSM, XRD, EDX, ICP and TGA. Furthermore, the recycled catalyst can be reused for several runs and is economically effective.
Direct Synthesis of N-Difluoromethyl-2-pyridones from Pyridines
Zhou, Sen,Hou, Xiaoya,Yang, Kai,Guo, Minjie,Zhao, Wentao,Tang, Xiangyang,Wang, Guangwei
, p. 6879 - 6887 (2021/05/29)
A novel method for the synthesis of N-difluoromethyl-2-pyridones was described. This protocol enables the synthesis of N-difluoromethyl-2-pyridones from readily available pyridines using mild reaction conditions that are compatible with a wide range of functional groups. The preliminary mechanistic study revealed that N-difluoromethylpyridinium salts were the key intermediates to complete this conversion.
