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67436-13-9

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A comprehensive one-pot synthesis of protected cysteine and selenocysteine SPPS derivatives
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.
Flemer, Stevenson
p. 1257 - 1264
(2015/04/14)

Peptide Synthesis. Part 6. Protection of the Sulphydryl Group of Cysteine in Solid-phase Synthesis using Nα-Fluorenylmethoxycarbonylamino Acids. Linear Oxytocin Derivatives
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.
Atherton, Eric,Pinori, Masimo,Sheppard, Robert C.
p. 2057 - 2064
(2007/10/02)

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Chemical Properties

Appearance/Colour :White to off white powder
Melting Point: 135-137 °C
Boiling Point: 603.4 °C at 760 mmHg
Flash Point:318.7 °C
Density: 1.237 g/cm³
Storage Temp.:2-8°C
Vapor Pressure: 2.08E-15mmHg at 25°C
Refractive Index: 1.599
PKA: 3.49±0.10(Predicted)
BRN: 4577031
PSA: 100.93000
LogP: 4.90090

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