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CAS 213383-02-9

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4-tert-butyl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine

Description:
4-tert-butyl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine, commonly referred to as Fmoc-L-phenylalanine tert-butyl ester, is a derivative of the amino acid phenylalanine. This compound features a tert-butyl group, which enhances its hydrophobic characteristics, and an Fmoc (fluorenylmethyloxycarbonyl) protecting group, commonly used in peptide synthesis to protect the amino group of amino acids. The presence of the fluorenyl group contributes to its stability and solubility in organic solvents, making it suitable for various synthetic applications. The compound is typically used in solid-phase peptide synthesis, where the Fmoc group can be easily removed under basic conditions, allowing for the sequential addition of amino acids. Its structure includes a phenylalanine backbone, which is essential for the formation of peptides and proteins, and the tert-butyl group aids in steric hindrance, influencing the compound's reactivity and interaction with other molecules. Overall, this compound is significant in the field of organic chemistry and biochemistry, particularly in the synthesis of complex peptides.
Formula:C28H29NO4
InChI:InChI=1/C28H29NO4/c1-28(2,3)19-14-12-18(13-15-19)16-25(26(30)31)29-27(32)33-17-24-22-10-6-4-8-20(22)21-9-5-7-11-23(21)24/h4-15,24-25H,16-17H2,1-3H3,(H,29,32)(H,30,31)/t25-/m0/s1
SMILES:CC(C)(C)c1ccc(cc1)C[C@@H](C(=O)O)N=C(O)OCC1c2ccccc2c2ccccc12
Synonyms:
  • Fmoc-L-4-tetr-Butylphenylalanine
  • Fmoc-4-tert-butyl-L-phenylalanine
  • Fmoc-L-4-Tert-Butyl-Phe
  • Fmoc-Phe(4-tBu)-OH
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