56-17-7Relevant articles and documents
Synthesis of reversible cyclic peptides
Ortiz-Acevedo, Alfonso,Dieckmann, Gregg R.
, p. 6795 - 6798 (2004)
Reversible cyclic peptides were synthesized by introducing a disulfide bond into the backbone of a peptide containing alternating d/l amino acids. The peptides exist in two distinct conformations (linear/cyclic) that are controlled by reduction/oxidation of the disulfide bond. A novel approach for the synthesis of cyclic peptides that can exist in either linear or cyclized conformations is described. Synthesis of the peptides was achieved via a modified solid phase methodology. The reversible linear/cyclized (i.e., open/closed) states are controlled via the reduction/oxidation of a disulfide bond incorporated into the backbone of the peptide chain.
Stereoselective synthesis of 4-substituted azetidine-2,3-diones by ring opening of 1,3-thiazolidine-derived spiro-β-lactams
Cremonesi, Giuseppe,Croce, Piero Dalla,Fontana, Francesco,Rosa, Concetta La
, p. 554 - 561 (2008/09/20)
New 3-heterocycle substituted 1,3-thiazolidine-derived 4-spiro-β-lactams with a relative trans-configuration were stereoselectively synthesised by means of a Staudinger ketene-imine reaction between the ketene generated from the (2S,4R)-1,3-thiazolidine-2,3,4-tricarboxylic acid 3-(1,1-dimethylethyl) 4-methyl ester 1 and imines 2b-e. The 1,3-thiazolidine-derived 4-spiro-β-lactams were transformed into the corresponding enantiomerically pure 4-heterocycle substituted azetidine-2,3-diones by means of an oxidative cleavage of the 1,3-thiazolidine ring. The opening of the 1,3-thiazolidine ring was studied under different experimental conditions and a consistent mechanism is proposed.
Organosulfur compounds as pre-exposure therapy for threat agents.
Ternay Jr.,Brzezinska,Sorokin,Cook,Lyaschenko
, p. S31-34 (2007/10/03)
A series of symmetric (Ar-S-S-Ar) and unsymmetric (Ar-S-S-CH2CH2NH3+Cl-) disulfides have been prepared and evaluated as potential cyanoprotective agents. Target compounds have been prepared by known methods and/or methods developed by us specifically for this program, e.g. reaction of a thiol with 2,2'-dithiobis(benzothiazole) (BT-S-S-BT) followed by reaction with a second thiol. Both 4-methoxyphenyl disulfide and 2-aminoethyl-4-methoxyphenyl disulfide hydrochloride are cyanoprotective against 2-LD50 of injected cyanide. Evaluation of both symmetric and unsymmetric related disulfides indicates that structural requirements for cyanoprotective activity are stringent and strongly suggest that protection is enzyme mediated. In addition to cyanoprotective action, initial results suggest that unsymmetric disulfides may evolve into effective antimustard agents.
