61925-77-7Relevant 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.
Sulfur-containing amino acid derivatives
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, (2008/06/13)
PCT No. PCT/JP97/03124 Sec. 371 Date Mar. 1, 1999 Sec. 102(e) Date Mar. 1, 1999 PCT Filed Sep. 5, 1997 PCT Pub. No. WO98/09943 PCT Pub. Date May 12, 1998A sulfur-containing amino acid compound having a high inhibitory activity on LTA4 hydrolase which is r
Two new procedures for the introduction of benzyl-type protecting groups for thiols
Richter, Lutz S.,Marsters Jr., James C.,Gadek, Thomas R.
, p. 1631 - 1634 (2007/10/02)
Two new methods for the benzylation of thiols are described: a) direct-S- alkylation with para-substituted benzylic cations; and b) reductive S- alkylations of 2-aminothiols. Both methods provide efficient routes for the introduction of benzyl-type protecting groups in high yields.
Synthetic studies on quinoxaline antibiotics. III. Synthesis of nortriostin A, a triostin A analog lacking N-methyl groups on the cystine and valine residues
Shin,Inouye,Higuchi,Kyogoki
, p. 2211 - 2215 (2007/10/02)
Nortriostin A, which is an analog of a cyclic octadepsipeptide antibiotic triostin A and contains one cystine and two valine residues substituted for the N,N'-dimethylcystine and N-methylvaline residues of the antibiotic, was synthesized with Z-D-Ser[Boc-Ala-Cys(MeBzl)-Val]-OH and Z-D-Ser[H-Ala-Cys(MeBZ)-Val]-OTce as key intermediates. The synthetic analog showed no antimicrobial activity at a concentration of 100 μg/ml and was found to exist as a single structure in solution as examined by 1H-NMR spectroscopy. The latter observation suggests that the conformer equilibrium known to occur with triostin A is a consequence of the presence of N-methyl peptide bonds in the antibiotic molecule. Nortriostin A, which is an analog of a cyclic octadepsipeptide antibiotic triostin A and contains one cystine and two valine residues substituted for the N,N prime -dimethylcystine and N-methylvaline residues of the antibiotic, was synthesized with Z-//D-Ser left bracket Boc-Ala-Cys(MeBzl)-Val right bracket -OH and Z-//D-Ser left bracket H-Ala-Cys(MeBzl)-Val right bracket -OTce as key intermediates. The synthetic analog showed no antimicrobial activity at a concentration of 100 mu g/ml and was found to exist as a single structure in solution as examined by **1H-NMR spectroscopy. The latter observation suggests that the conformer equilibrium known to occur with triostin A is a consequence of the presence of N-methyl peptide bonds in the antibiotic molecule.
