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CAS 908846-99-1

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N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-6-methyl-L-tryptophan

Description:
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-6-methyl-L-tryptophan, commonly referred to as Fmoc-6-methyl-L-tryptophan, is a derivative of the amino acid tryptophan, 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 6-methyl group on the tryptophan side chain enhances its hydrophobicity and can influence the folding and stability of peptides. The Fmoc group is typically removed under basic conditions, allowing for the subsequent coupling of additional amino acids. This compound is generally stable under standard laboratory conditions but should be handled with care due to the potential for reactivity associated with the functional groups present. Its unique structure and properties make it valuable in the field of biochemistry and pharmaceutical research, particularly in the development of peptide-based therapeutics.
Formula:C27H24N2O4
InChI:InChI=1S/C27H24N2O4/c1-16-10-11-18-17(14-28-24(18)12-16)13-25(26(30)31)29-27(32)33-15-23-21-8-4-2-6-19(21)20-7-3-5-9-22(20)23/h2-12,14,23,25,28H,13,15H2,1H3,(H,29,32)(H,30,31)/t25-/m0/s1
InChI key:InChIKey=AZYYHRQGDYITPE-VWLOTQADSA-N
SMILES:C(OC(N[C@@H](CC=1C=2C(NC1)=CC(C)=CC2)C(O)=O)=O)C3C=4C(C=5C3=CC=CC5)=CC=CC4
Synonyms:
  • L-Tryptophan, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-6-methyl-
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-6-methyl-L-tryptophan
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