N-α-(9-Fluorenylmethoxycarbonyl)-(3,4-propylenedioxy)-L-DOPA
Need Assistance?
  • US & Canada:
    +
  • UK: +

N-α-(9-Fluorenylmethoxycarbonyl)-(3,4-propylenedioxy)-L-DOPA

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

N-α-(9-Fluorenylmethoxycarbonyl)-(3,4-propylenedioxy)-L-DOPA (CAS# 852288-18-7 ) is a useful research chemical.

Category
Fmoc-Amino Acids
Catalog number
BAT-005380
CAS number
852288-18-7
Molecular Formula
C27H25NO6
Molecular Weight
459.50
N-α-(9-Fluorenylmethoxycarbonyl)-(3,4-propylenedioxy)-L-DOPA
IUPAC Name
(2S)-3-(2,2-dimethyl-1,3-benzodioxol-5-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-DOPA(3,4-diOxProp)-OH; Fmoc-DOPA(acetonide)-OH; N-α-(9-Fluorenylmethoxycarbonyl)-L-(3,4-acetonide-dihydroxy)phenylalanine; (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-((diphenyl(p-tolyl)methyl)amino)hexanoic acid; Fmoc-D-Lys(Mtt)-OH; Fmoc-3,4-dihydroxy-L-phenylalanine, acetonide protected; Fmoc-DOPA-OH,acetonide protected
Appearance
White powder
Purity
≥ 99 % (HPLC)
Density
1.302 g/cm3
Boiling Point
663.1±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C27H25NO6/c1-27(2)33-23-12-11-16(14-24(23)34-27)13-22(25(29)30)28-26(31)32-15-21-19-9-5-3-7-17(19)18-8-4-6-10-20(18)21/h3-12,14,21-22H,13,15H2,1-2H3,(H,28,31)(H,29,30)/t22-/m0/s1
InChI Key
SHZLOTJPHMTVDI-QFIPXVFZSA-N
Canonical SMILES
CC1(OC2=C(O1)C=C(C=C2)CC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)C
1.Convenient Synthesis of Acetonide Protected 3,4-Dihydroxyphenylalanine (DOPA) for Fmoc Solid-Phase Peptide Synthesis.
Liu Z1, Hu BH, Messersmith PB. Tetrahedron Lett. 2008 Sep 15;49(38):5519-5521.
We report a facile approach to the synthesis of acetonide and Fmoc protected 3,4-dihydroxyphenylalanine (DOPA), Fmoc-DOPA(acetonide)-OH. By protecting the amino group of DOPA with a phthaloyl group and the carboxyl group as a methyl ester, acetonide protection of the catechol of DOPA derivative was realized in the presence of p-toluenesulfonic acid. Following removal of protecting groups, the intermediate was converted to Fmoc-DOPA(acetonide)-OH, which was successfully incorporated into a short DOPA-containing peptide, derived from marine tubeworm cement proteins Pc1 and Pc2.
Online Inquiry
Verification code
Inquiry Basket