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CAS 118488-18-9

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fmoc-O-tert-butyl-D-tyrosine

Description:
Fmoc-O-tert-butyl-D-tyrosine is a protected form of the amino acid D-tyrosine, commonly used in peptide synthesis. The "Fmoc" (9-fluorenylmethoxycarbonyl) group serves as a protective group for the amino functionality, allowing for selective reactions without interfering with the amino acid's reactivity. The "O-tert-butyl" designation indicates that the hydroxyl group of the tyrosine side chain is also protected, enhancing the stability and solubility of the compound during synthesis. This compound is typically a white to off-white solid and is soluble in organic solvents like dichloromethane and dimethylformamide, but less soluble in water. Its structure allows for the introduction of D-tyrosine into peptides while maintaining the integrity of the amino acid's functional groups until deprotection is desired. The use of Fmoc chemistry is prevalent in solid-phase peptide synthesis, making this compound valuable in the field of medicinal chemistry and biochemistry for the development of peptide-based therapeutics.
Formula:C28H29NO5
InChI:InChI=1/C28H29NO5/c1-28(2,3)34-19-14-12-18(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-/m1/s1
InChI key:JAUKCFULLJFBFN-RUZDIDTESA-N
SMILES:CC(C)(C)Oc1ccc(cc1)C[C@H](C(=O)O)N=C(O)OCC1c2ccccc2c2ccccc12
Synonyms:
  • Fmoc-D-Tyr(tBu)-OH
  • Fmoc-D-Tyr(But)-OH
  • O-tert-butyl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-tyrosine
  • Fmoc-D-Tyr(OtBu)-OH
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