2,2 -Dipyridyl disulphide

Cathepsin B (from human liver) [9025-22-7] [EC 3.4.22.1]. Purified by affinity chromatography on the semicarbazone of Gly-Phe-glycinal-linked to Sepharose 4B, with elution by 2,2 -dipyridyl disulphide [Rich et al. BJ 235 731 1986]. 

K. Broctdehurst, . M. Crook, and M. KJentan. The mutability of stem bromelain evidence for perturbation by structural transitions of (he parameters that characterize the reaction of the essential thiol group of bromelain with 2,2 -dipyridyl disulphide. J. Biochem. 128379 (1972). 

A new synthesis of ( )-carpamic acid (33) has been reported. A new synthesis of carpaine (34), utilizing a procedure developed recently for the synthesis of macrocyclic lactones,has been described briefly the key reaction was between N-benzyloxycarbonylcarpamic acid (35), 2,2 -dipyridyl disulphide, and triphenyl-phosphine, affording NN -bisbenzyloxycarbonylcarpaine in better than 50% yield. ... 

The study of methods to enhance ester- or amide-bond formation continues to provide much stimulus. A Japanese group, continuing their researches in this vein, have reported on amide and ester bond formation via oxidation-reduction condensation by use of 2,2 -dipyridyl disulphide as oxidant the reduced reagent, 2-mercaptopyridine, isomerizes to the more stable, less reactive thione form. This is shown in Scheme 29. 

The method of esterification, based on the double activation route to macro-lides, mentioned earlier (Scheme 26, p. 135) has been found to be equally effective in the formation of amides from carboxylic acids and primary or secondary amines. The well known method for amide bond formation in peptide synthesis using mixtures of triphenylphosphine and 2,2 -dipyridyl disulphide has been modified by employing polymer-bound triphenylphosphine. In a similar vein, mixtures of triphenylphosphine and carbon tetrachloride have been reported to be useful in the formation of amide linkages in peptide synthesis.A similar method using polymer-bound phosphine with carbon tetrachloride and tiiethylamine has also been reported. ... 

Bewick A, Mellor JM, Milano D, Owton WM. Addition to alkenes via metal ion-promoted oxidation of 2,2 -dipyridyl disulphide and bis-(2-aminophenyl) disulphide. /. Chem. Soc., Perkin Trans. 11985 1045-1048. 

The reaction of dipyridyl disulphide with triphenylphosphine to give the stable phosphonium salt (51) has been used in new methods of phosphorylation (reaction A), in peptide synthesis (reaction B), and in the formation of active esters of cx-amino-acids (reaction C). These reactions appear to have synthetic potential. 

Pyridine 1-oxide reacts with adamantane-1-thiol in acetic anhydride to give 2- and 3-(l-adamantanethio)pyridines and their tetrahydropyridine analogues. Corresponding butylthio-substituted pyridines are obtained using Bu SH or Bu SH in this reaction in the presence of a chloroformic acid derivative. No complications arise in the use of 3-bromopyridine 1-oxide and KSH for the synthesis of 3,3 -dipyridyl sulphide. 2-Methyl- or 2-phenyl-pyridine is converted into its 5-alkylthio-homologue by reaction of the pyridine-MeLi adduct with a dialkyl disulphide. ... 

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