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CAS 112380-10-6

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N(alpha)-fmoc-N(im)-tosyl-L-histidine

Description:
N(alpha)-Fmoc-N(im)-tosyl-L-histidine is a derivative of the amino acid histidine, characterized by the presence of a fluorenylmethyloxycarbonyl (Fmoc) protecting group at the alpha-amino position and a tosyl (p-toluenesulfonyl) group at the imidazole nitrogen. This compound is typically used in peptide synthesis, particularly in solid-phase peptide synthesis, due to its ability to protect functional groups while allowing for selective reactions. The Fmoc group is favored for its stability under basic conditions and ease of removal under mild conditions, making it suitable for sequential coupling reactions. The tosyl group enhances the electrophilicity of the imidazole nitrogen, facilitating further chemical transformations. N(alpha)-Fmoc-N(im)-tosyl-L-histidine is soluble in organic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF), and it exhibits characteristics typical of histidine derivatives, including potential for coordination with metal ions and involvement in enzyme catalysis. Its unique structure allows for specific applications in biochemistry and medicinal chemistry.
Formula:C28H25N3O6S
InChI:InChI=1/C28H25N3O6S/c1-18-10-12-20(13-11-18)38(35,36)31-15-19(29-17-31)14-26(27(32)33)30-28(34)37-16-25-23-8-4-2-6-21(23)22-7-3-5-9-24(22)25/h2-13,15,17,25-26H,14,16H2,1H3,(H,30,34)(H,32,33)/t26-/m0/s1
SMILES:Cc1ccc(cc1)S(=O)(=O)n1cc(C[C@@H](C(=O)O)N=C(O)OCC2c3ccccc3c3ccccc23)nc1
Synonyms:
  • Fmoc-His(Tos)-OH
  • N-[(9H-fluoren-9-ylmethoxy)carbonyl]-1-[(4-methylphenyl)sulfonyl]-L-histidine
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