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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

Specification
Reference Reading

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.