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CAS 1145678-75-6

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N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-methyl-L-tyrosine

Description:
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-methyl-L-tyrosine, commonly referred to as Fmoc-2-methyl-L-tyrosine, is a derivative of the amino acid tyrosine, modified with a fluorenylmethoxycarbonyl (Fmoc) protecting group. This compound is characterized by its use in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS), where the Fmoc group serves as a temporary protective group for the amino group of the amino acid. The presence of the methyl group at the 2-position of the tyrosine side chain enhances its hydrophobicity, which can influence the folding and stability of peptides. The Fmoc group is stable under basic conditions and can be removed under mild acidic conditions, allowing for selective deprotection during peptide assembly. This compound is typically a white to off-white solid and is soluble in organic solvents such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO). Its unique structure and properties make it valuable in the field of biochemistry and pharmaceutical research for the synthesis of bioactive peptides.
Formula:C25H23NO5
InChI:InChI=1S/C25H23NO5/c1-15-12-17(27)11-10-16(15)13-23(24(28)29)26-25(30)31-14-22-20-8-4-2-6-18(20)19-7-3-5-9-21(19)22/h2-12,22-23,27H,13-14H2,1H3,(H,26,30)(H,28,29)/t23-/m0/s1
InChI key:InChIKey=MEFNXNKFGAIWBC-QHCPKHFHSA-N
SMILES:C(OC(N[C@@H](CC1=C(C)C=C(O)C=C1)C(O)=O)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3
Synonyms:
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-methyl-L-tyrosine
  • L-Tyrosine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methyl-
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