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CAS 20898-44-6

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N(alpha)-boc-N(im)-benzyl-L-histidine

Description:
N(alpha)-Boc-N(im)-benzyl-L-histidine is a derivative of the amino acid histidine, characterized by the presence of a tert-butyloxycarbonyl (Boc) protecting group at the alpha-amino group and a benzyl group at the imidazole nitrogen. This compound is typically used in peptide synthesis and as an intermediate in the preparation of more complex molecules. It features a chiral center, making it optically active, and its structure includes both hydrophilic and hydrophobic regions, which can influence its solubility and interaction with biological systems. The Boc group serves as a protective moiety that can be removed under acidic conditions, allowing for further functionalization of the histidine residue. The benzyl substitution enhances the lipophilicity of the molecule, potentially affecting its biological activity and interactions. Overall, N(alpha)-Boc-N(im)-benzyl-L-histidine is valuable in synthetic organic chemistry and biochemistry, particularly in the development of pharmaceuticals and peptide-based therapeutics.
Formula:C18H23N3O4
InChI:InChI=1/C18H23N3O4/c1-18(2,3)25-17(24)20-15(16(22)23)9-14-11-21(12-19-14)10-13-7-5-4-6-8-13/h4-8,11-12,15H,9-10H2,1-3H3,(H,20,24)(H,22,23)/t15-/m0/s1
InChI key:InChIKey=OUHPNBGKEMHUCQ-HNNXBMFYSA-N
SMILES:CC(C)(C)OC(=N[C@@H](Cc1cn(Cc2ccccc2)cn1)C(=O)O)O
Synonyms:
  • (2S)-3-(1-Benzyl-1H-imidazol-4-yl)-2-[[(tert-butoxy)carbonyl]amino]propanoic acid
  • (2S)-3-(1-Benzylimidazol-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
  • 1-benzyl-N-(tert-butoxycarbonyl)-L-histidine
  • 1-benzyl-N-(tert-butoxycarbonyl)histidine
  • <span class="text-smallcaps">L</span>-Histidine, N-[(1,1-dimethylethoxy)carbonyl]-1-(phenylmethyl)-
  • Boc-<span class="text-smallcaps">L</span>-his(bn)-oh
  • Boc-His(Bzl)-OH
  • Histidine, 1-benzyl-N-carboxy-, N-tert-butyl ester, <span class="text-smallcaps">L</span>-
  • N-[(1,1-Dimethylethoxy)carbonyl]-1-(phenylmethyl)-<span class="text-smallcaps">L</span>-histidine
  • N-tert-Butoxycarbonyl-1-phenylmethyl-<span class="text-smallcaps">L</span>-histidine
  • See more synonyms
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