Fmoc-3,4-dihydroxy-L-phenylalanine

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Catalog Number
ACM137018930
Product Name
Fmoc-3,4-dihydroxy-L-phenylalanine
Structure
Structure
CAS
137018-93-0
Category
Amino Acids
Description
Fmoc-DOPA is a synthetic derivative of L-DOPA, a naturally occurring amino acid that is a precursor to dopamine and other catecholamines. It is synthesized by attaching a fluorenylmethoxycarbonyl (Fmoc) group to the amino group of DOPA, which results in increased solubility and stability. Fmoc-DOPA has been widely used in peptide synthesis and as a building block in the preparation of bioconjugates due to its unique chemical and physical properties.
Synonyms
(R)-Fmoc-nipecotic acid, (R)-N-Fmoc-piperidine-3-carboxylic acid, (r)-fmoc-piperidine-3-carboxylic acid, N-(9-fluorenylmethyloxycarbonyl)-3,4-dihydroxy-L-phenylalanine, (R)-Fmoc-Nip-OH, (r)-1-fmoc-piperidine-3-carboxylic acid, Fmoc-L-DOPA
IUPAC Name
(2S)-3-(3,4-dihydroxyphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Molecular Weight
419.4
Molecular Formula
C24H21NO6
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC(=C(C=C4)O)O)C(=O)O
InChI
1S/C24H21NO6/c26-21-10-9-14(12-22(21)27)11-20(23(28)29)25-24(30)31-13-19-17-7-3-1-5-15(17)16-6-2-4-8-18(16)19/h1-10,12,19-20,26-27H,11,13H2,(H,25,30)(H,28,29)/t20-/m0/s1
InChI Key
NIJSCWCPASSJPI-FQEVSTJZSA-N
Application
Fmoc-DOPA has been widely used in peptide synthesis and as a building block in the preparation of bioconjugates. It has also been studied for its potential use in tissue engineering and regenerative medicine, due to its ability to promote cell adhesion and differentiation. Fmoc-DOPA has also been studied for its potential use in drug delivery, due to its ability to cross the blood-brain barrier.
Exact Mass
419.137
Functional Group
Fmoc
HS Code
2924299090
LogP
3.8366
MDL Number
MFCD02682263
PSA
119.58
Storage Temperature
4 ℃
Type
Unusual Amino Acids, Analogs of Phenylalanine and Tyrosine
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