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CAS 202920-22-7

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N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-1-methyl-L-histidine

Description:
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-1-methyl-L-histidine, commonly referred to as Fmoc-1-methyl-L-histidine, is a derivative of the amino acid histidine, modified for use in peptide synthesis. This compound features a fluorenylmethoxycarbonyl (Fmoc) protecting group, which is widely utilized in solid-phase peptide synthesis due to its stability under basic conditions and ease of removal under acidic conditions. The presence of the methyl group at the 1-position of the histidine side chain alters its properties, potentially influencing the compound's hydrophobicity and steric effects. Fmoc-1-methyl-L-histidine is characterized by its ability to participate in peptide bond formation, making it valuable in the synthesis of peptides and proteins for research and therapeutic applications. Its molecular structure includes aromatic and aliphatic components, contributing to its unique chemical behavior. Additionally, the compound is typically handled under standard laboratory conditions, with considerations for proper storage and safety protocols due to its chemical nature.
Formula:C22H21N3O4
InChI:InChI=1S/C22H21N3O4/c1-25-11-14(23-13-25)10-20(21(26)27)24-22(28)29-12-19-17-8-4-2-6-15(17)16-7-3-5-9-18(16)19/h2-9,11,13,19-20H,10,12H2,1H3,(H,24,28)(H,26,27)/t20-/m0/s1
InChI key:InChIKey=SLWOFHRSEVVUHM-FQEVSTJZSA-N
SMILES:C(OC(N[C@@H](CC1=CN(C)C=N1)C(O)=O)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3
Synonyms:
  • L-Histidine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-1-methyl-
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-1-methyl-L-histidine
  • (2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(1-methylimidazol-4-yl)propanoic acid
  • (2S)-2-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)-3-(1-methyl-1H-imidazol-4-yl)propanoic acid
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