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FMOC-D-3,4-DIMETHOXYPHENYLALANINE - CAS 218457-81-9

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Category
Main Product
Product Name
FMOC-D-3,4-DIMETHOXYPHENYLALANINE
Catalog Number
218457-81-9
Synonyms
RARECHEM EM WB 0122;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-(3,4-DIMETHOXY)-D-PHENYLALANINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-(3-METHOXY,4-METHYL)-D-TYROSINE;(R)-3-(3,4-DIMETHOXY-PHENYL)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PROPIONIC ACID;FMOC-3,4-DIM
CAS Number
218457-81-9
Molecular Weight
447.48
Molecular Formula
C26H25NO6
COA
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MSDS
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Canonical SMILES
COC1=C(C=C(C=C1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)OC
InChI
InChI=1S/C26H25NO6/c1-31-23-12-11-16(14-24(23)32-2)13-22(25(28)29)27-26(30)33-15-21-19-9-5-3-7-17(19)18-8-4-6-10-20(18)21/h3-12,14,21-22H,13,15H2,1-2H3,(H,27,30)(H,28,29)/t22-/m1/s1
InChIKey
XJRGWWYKCGWQHH-JOCHJYFZSA-N
Structure
CAS 218457-81-9 FMOC-D-3,4-DIMETHOXYPHENYLALANINE
Specification
Purity
95%
Storage
Store at 0ºC
Reference Reading
1.Structural optimization of SadA, an Fe(II)- and α-ketoglutarate-dependent dioxygenase targeting biocatalytic synthesis of N-succinyl-L-threo-3,4-dimethoxyphenylserine.
Qin HM1, Miyakawa T1, Nakamura A1, Hibi M2, Ogawa J3, Tanokura M4. Biochem Biophys Res Commun. 2014 Aug 8;450(4):1458-61. doi: 10.1016/j.bbrc.2014.07.008. Epub 2014 Jul 10.
L-threo-3,4-Dihydroxyphenylserine (l-DOPS, Droxidopa) is a psychoactive drug and synthetic amino acid precursor that acts as a prodrug to the neurotransmitters. SadA, a dioxygenase from Burkholderia ambifaria AMMD, is an Fe(II)- and α-ketoglutarate (KG)-dependent enzyme that catalyzes N-substituted branched-chain or aromatic l-amino acids. SadA is able to produce N-succinyl-l-threo-3,4-dimethoxyphenylserine (NSDOPS), which is a precursor of l-DOPS, by catalyzing the hydroxylation of N-succinyl-3,4-dimethoxyphenylalanine (NSDOPA). However, the catalytic activity of SadA toward NSDOPS is much lower than that toward N-succinyl branched-chain l-amino acids. Here, we report an improved biocatalytic synthesis of NSDOPS with SadA. Structure-based protein engineering was applied to improve the α-KG turnover activity for the synthesis of NSDOPS. The G79A, G79A/F261W or G79A/F261R mutant showed a more than 6-fold increase in activity compared to that of the wild-type enzyme.
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