73724-43-3Relevant articles and documents
A comprehensive one-pot synthesis of protected cysteine and selenocysteine SPPS derivatives
Flemer, Stevenson
, p. 1257 - 1264 (2015/04/14)
A proof-of-principle methodology is presented in which all commercially-available cysteine (Cys) and selenocysteine (Sec) solid phase peptide synthesis (SPPS) derivatives are synthesized in high yield from easily prepared protected dichalcogenide precursors. A Zn-mediated biphasic reduction process applied to a series of four bis-Nα-protected dichalcogenide compounds allows facile conversion to their corresponding thiol and selenol intermediates followed by insitu S- or Se-alkylation with various electrophiles to directly access twenty one known Cys and Sec SPPS derivatives. Most of these derivatives were able to be precipitated in crude form out of petroleum ether in sufficient purity for direct use as peptide building blocks. Subsequent incorporation of these derivatives into peptide models nicely illustrates their viability and applicability toward SPPS.
Efficient microwave-assisted synthesis of unsymmetrical disulfides
Gormer, Kristina,Waldmann, Herbert,Triola, Gemma
supporting information; experimental part, p. 1811 - 1813 (2010/05/17)
"Chemical equation presented" An efficient synthesis of unsymmetrical disulfides exemplified for cysteines and penicillamines is described. The use of dimethyl sulfoxide mediated oxidation accelerated by microwave irradiation afforded various unsymmetrical disulfides in one step and in high yields.
Peptide Synthesis. Part 6. Protection of the Sulphydryl Group of Cysteine in Solid-phase Synthesis using Nα-Fluorenylmethoxycarbonylamino Acids. Linear Oxytocin Derivatives
Atherton, Eric,Pinori, Masimo,Sheppard, Robert C.
, p. 2057 - 2064 (2007/10/02)
The Nα-fluorenylmethoxycarbonyl derivatives of S-acetamidomethyl-, S-t-butyl-, and S-S-t-butyl-cysteine have been prepared and used in solid-phase peptide synthesis on polar, poly(dimethylacrylamide) supports.All three derivatives proved suitable as judged by synthesis of the linear oxytocin nonapeptide amide sequence.
