Fmoc-L-glutamic acid α-methyl ester
Need Assistance?
  • US & Canada:
    +
  • UK: +

Fmoc-L-glutamic acid α-methyl ester

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

Category
Fmoc-Amino Acids
Catalog number
BAT-001985
CAS number
145038-49-9
Molecular Formula
C21H21NO6
Molecular Weight
383.36
IUPAC Name
(4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-methoxy-5-oxopentanoic acid
Synonyms
Fmoc-L-Glu-Ome; (4S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-5-methoxy-5-oxopentanoicacid
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.296±0.06 g/cm3(Predicted)
Melting Point
120-140°C
Boiling Point
630.6±55.0 °C(Predicted)
Storage
Store at RT
InChI
InChI=1S/C21H21NO6/c1-27-20(25)18(10-11-19(23)24)22-21(26)28-12-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,17-18H,10-12H2,1H3,(H,22,26)(H,23,24)/t18-/m0/s1
InChI Key
GVVDKFNHFXLOQY-SFHVURJKSA-N
Canonical SMILES
COC(=O)C(CCC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
1. Catalytic asymmetric synthesis of α-methyl-p-boronophenylalanine
Shingo Harada, Ryota Kajihara, Risa Muramoto, Promsuk Jutabha, Naohiko Anzai, Tetsuhiro Nemoto Bioorg Med Chem Lett. 2018 Jun 1;28(10):1915-1918. doi: 10.1016/j.bmcl.2018.03.075. Epub 2018 Mar 28.
p-Boronophenylalanine (l-BPA) is applied in clinical settings as a boron carrier for boron neutron capture therapy (BNCT) to cure malignant melanomas. Structural modification or derivatization of l-BPA, however, to improve its uptake efficiency into tumor cells has scarcely been investigated. We successfully synthesized (S)-2-amino-3-(4-boronophenyl)-2-methylpropanoic acid in enantioenriched form as a novel candidate molecule for BNCT. Key steps to enhance the efficiency of this synthesis were enantioselective alkylation of N-protected alanine tert-butyl ester with a Maruoka catalyst and Miyaura borylation reaction to install the boron functionality.
2. Microbial/enzymatic synthesis of chiral drug intermediates
R N Patel Adv Appl Microbiol. 2000;47:33-78. doi: 10.1016/s0065-2164(00)47001-2.
Biocatalytic processes were used to prepare chiral intermediates for pharmaceuticals. These include the following processes. Enzymatic synthesis of [4S-(4a,7a,10ab)]1-octahydro-5-oxo-4-[[(phenylmethoxy) carbonyl]amino]-7H-pyrido-[2,1-b] [1,3]thiazepine-7-carboxylic acid methyl ester (BMS-199541-01), a key chiral intermediate for synthesis of a new vasopeptidase inhibitor. Enzymatic oxidation of the epsilon-amino group of lysine in dipeptide dimer N2-[N[[(phenylmethoxy)carbonyl] L-homocysteinyl] L-lysine)1,1-disulfide (BMS-201391-01) to produce BMS-199541-01 using a novel L-lysine epsilon-aminotransferase from S. paucimobilis SC16113 was demonstrated. This enzyme was overexpressed in E. coli, and a process was developed using recombinant enzyme. The aminotransferase reaction required alpha-ketoglutarate as the amine acceptor. Glutamate formed during this reaction was recycled back to alpha-ketoglutarate by glutamate oxidase from S. noursei SC6007. Synthesis and enzymatic conversion of 2-keto-6-hydroxyhexanoic acid 5 to L-6-hydroxy norleucine 4 was demonstrated by reductive amination using beef liver glutamate dehydrogenase. To avoid the lengthy chemical synthesis of ketoacid 5, a second route was developed to prepare the ketoacid by treatment of racemic 6-hydroxy norleucine (readily available from hydrolysis of 5-(4-hydroxybutyl) hydantoin, 6) with D-amino acid oxidase from porcine kidney or T. variabilis followed by reductive amination to convert the mixture to L-6-hydroxynorleucine in 98% yield and 99% enantiomeric excess. Enzymatic synthesis of (S)-2-amino-5-(1,3-dioxolan-2-yl)-pentanoic acid (allysine ethylene acetal, 7), one of three building blocks used for synthesis of a vasopeptidase inhibitor, was demonstrated using phenylalanine dehydrogenase from T. intermedius. The reaction requires ammonia and NADH. NAD produced during the reaction was recycled to NADH by oxidation of formate to CO2 using formate dehydrogenase.
Online Inquiry
Verification code
Inquiry Basket