L-Glutamic acid α-tert-butyl ester
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L-Glutamic acid α-tert-butyl ester

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L-Glutamic acid α-tert-butyl ester is an ester of L-Glutamic acid used in the synthesis of enantiopure isotopomers of amino acids.

Category
γ−Amino acids
Catalog number
BAT-004249
CAS number
45120-30-7
Molecular Formula
C9H17NO4
Molecular Weight
203.20
L-Glutamic acid α-tert-butyl ester
Size Price Stock Quantity
5 g $199 In stock
IUPAC Name
(4S)-4-amino-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid
Synonyms
L-Glu-OtBu; (S)-4-Amino-5-(tert-butoxy)-5-oxopentanoic acid; L-Glutamic acid α-tert butyl ester
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.133±0.06 g/cm3
Melting Point
135-145 °C
Boiling Point
326.8±32.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H17NO4/c1-9(2,3)14-8(13)6(10)4-5-7(11)12/h6H,4-5,10H2,1-3H3,(H,11,12)/t6-/m0/s1
InChI Key
QVAQMUAKTNUNLN-LURJTMIESA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CCC(=O)O)N
1.L-Glutamic acid and L-lysine as useful building blocks for the preparation of bifunctional DTPA-like ligands.
Anelli PL1, Fedeli F, Gazzotti O, Lattuada L, Lux G, Rebasti F. Bioconjug Chem. 1999 Jan-Feb;10(1):137-40.
Bisalkylation of suitably protected L-glutamic acid and L-lysine derivatives with tert-butyl N-(2-bromoethyl)iminodiacetate 2, followed by deprotection of the omega functional group affords N, N-bis[2-[bis[2-(1, 1-dimethylethoxy)-2-oxoethyl]amino]ethyl]-L-glutamic acid 1-(1, 1-dimethylethyl) ester 4 and N2,N2-bis[2-[bis[2-(1, 1-dimethylethoxy)-2-oxoethyl]amino]ethyl]-L-lysine 1,1-dimethylethyl ester 7. Such compounds feature a carboxylic or an amino group, respectively, which are available for conjugation with a suitable partner via formation of an amide bond. The conjugates, which can be prepared in this way, contain a chelating subunit in which all five acetic residues of DTPA are available for the complexation of metal ions. Direct bisalkylation of glycine with 2 promptly gives N, N-bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]glycine 11. The latter allows to achieve conjugates in which the central acetic group of DTPA is selectively converted into an acetamide.
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