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CAS 61925-77-7

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boc-S-(4-methylbenzyl)-L-cysteine

Description:
Boc-S-(4-methylbenzyl)-L-cysteine is a derivative of the amino acid cysteine, characterized by the presence of a tert-butyloxycarbonyl (Boc) protecting group on the amino group and a 4-methylbenzyl group attached to the sulfur atom. This compound is typically used in peptide synthesis and medicinal chemistry due to its ability to protect functional groups during reactions. The Boc group is commonly employed to temporarily mask the amino group, facilitating selective reactions without interference. The 4-methylbenzyl substituent enhances the lipophilicity and steric properties of the molecule, which can influence its reactivity and biological activity. As a cysteine derivative, it retains the thiol (-SH) functionality, which is crucial for forming disulfide bonds and participating in redox reactions. The compound is generally stable under standard laboratory conditions but should be handled with care due to the potential reactivity of the thiol group. Its applications may extend to drug development, particularly in the design of peptide-based therapeutics.
Formula:C16H23NO4S
InChI:InChI=1/C16H23NO4S/c1-11-5-7-12(8-6-11)9-22-10-13(14(18)19)17-15(20)21-16(2,3)4/h5-8,13H,9-10H2,1-4H3,(H,17,20)(H,18,19)/t13-/m0/s1
SMILES:Cc1ccc(cc1)CSC[C@@H](C(=O)O)N=C(O)OC(C)(C)C
Synonyms:
  • Boc-Cys(Mbzl)-OH
  • Boc-Cys(pMeBzl)-OH
  • Boc-Cys(4-MeBzl)-OH
  • N-(tert-butoxycarbonyl)-S-(4-methylbenzyl)cysteine
  • N-(tert-butoxycarbonyl)-S-(4-methylbenzyl)-D-cysteine
  • N-(tert-butoxycarbonyl)-S-(4-methylbenzyl)-L-cysteine
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