Boc-L-glutamic acid α-methyl ester
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Boc-L-glutamic acid α-methyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-002768
CAS number
72086-72-7
Molecular Formula
C11H19NO6
Molecular Weight
261.40
Boc-L-glutamic acid α-methyl ester
IUPAC Name
(4S)-5-methoxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid
Synonyms
Boc-L-Glu-Ome; (S)-4-((tert-Butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid
Appearance
White to off-white crystalline powder
Purity
≥ 98% (HPLC)
Density
1.182±0.06 g/cm3(Predicted)
Melting Point
119-123°C
Boiling Point
428.4±40.0 °C(Predicted)
Storage
Store at-20 °C
InChI
InChI=1S/C11H19NO6/c1-11(2,3)18-10(16)12-7(9(15)17-4)5-6-8(13)14/h7H,5-6H2,1-4H3,(H,12,16)(H,13,14)/t7-/m0/s1
InChI Key
ZAYAFKXUQMTLPL-ZETCQYMHSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCC(=O)O)C(=O)OC

Boc-L-glutamic acid α-methyl ester, a derivative of a protected amino acid, holds a pivotal role in peptide synthesis and medicinal chemistry. Here are four key applications of this compound:

Peptide Synthesis: Serving as a foundational element in peptide synthesis, Boc-L-glutamic acid α-methyl ester stands out as a crucial building block. Imbued with a Boc (tert-butoxycarbonyl) protective group renowned for its exceptional stability in basic environments, this compound plays a critical role in the intricate dance of peptide chain assembly. The presence of the α-methyl ester facilitates the seamless integration of glutamic acid into peptides while upholding orthogonal protection strategies, ensuring the precise and efficient construction of peptides.

Medicinal Chemistry: Within the realm of drug development, Boc-L-glutamic acid α-methyl ester emerges as a key architect in the realm of prodrug design necessitating metabolic activation. The strategic ester linkage undergoes in vivo hydrolysis, freeing the biologically active drug compound. This innovative approach enhances the pharmacokinetic properties of drugs, fortifying their stability and absorption rates.

Polymer Chemistry: Venturing into the realm of polymer chemistry, Boc-L-glutamic acid α-methyl ester assumes a central role as a versatile component in the synthesis of functional polymers. Serving as a pivotal monomeric unit within polymeric materials, this compound finds application in tailoring drug delivery systems crafted for precise therapeutic release. The strategic ester linkages housed within the polymer structure can be selectively cleaved, enabling exact degradation and customized release profiles.

Bioconjugation: Expanding its utility even further, this compound takes center stage in bioconjugation processes, enabling the targeted modification of biomolecules like proteins and nucleic acids. The protective shroud of the Boc group safeguards the amino acid during conjugation, facilitating selective modification devoid of undesired side effects. This sophisticated technique empowers the creation of modified proteins imbued with enhanced properties, unlocking novel horizons in both research and therapeutic avenues.

1.Vitamin K-dependent carboxylase. In vitro inhibitory activity of cyclopentane and cyclohexane-derived analogues of glutamic acid and their conformational study by NMR and molecular dynamics in aqueous solution.
Larue V1, Gharbi-Benarous J, Acher F, Azerad R, Girault JP. J Pept Res. 1997 Jan;49(1):28-45.
The conformational analysis of four glutamic acid analogues containing a cyclopentyl or cyclohexyl ring, substituted in position 1 by a Boc-protected amino group and a methyl ester group and in position 3 by a free carboxylate group (6-9), has been carried out in an aqueous environment, by 1H and 13C NMR spectroscopy, and molecular dynamics (MD). These compounds have been shown to be weak competitive inhibitors (Ki approximately 20-65 mM) of the vitamin K-dependent carboxylation of Boc-Glu-OMe in rat liver microsomes independently of their ring size and stereochemical features. However, the cyclic trans isomers have been found more active than the cis ones, and Boc-trans-C5-OMe (9) is the most potent inhibitor in the series (cis and trans isomers are defined by the relative arrangement of the carboxyl functions). Such cyclic glutamyl derivatives may provide valuable informations on the preferred bioactive conformations of synthetic glutamyl substrates at the active site of the carboxylase.
2.Non-glutamate type pyrrolo[2,3-d]pyrimidine antifolates. II. Synthesis and antitumor activity of N5-substituted glutamine analogs.
Itoh F1, Yoshioka Y, Yukishige K, Yoshida S, Wajima M, Ootsu K, Akimoto H. Chem Pharm Bull (Tokyo). 1996 Aug;44(8):1498-509.
The glutamic acid moiety of N-[4-[3-(2,4-diamino-7H-pyrrolo[2, 3-d]pyrimidin-5-yl)propyl]benzoyl]-L-glutamic acid (1b, TNP-351) and related compounds was replaced with some N5-substituted glutamines. Antifolates (4A-S) were effectively prepared by coupling pyrrolo[2,3-d]pyrimidine carboxylic acids (11a, b) with some properly protected N5-substituted glutamine derivatives (10A-S), which were prepared by coupling Boc-Glu-OMe (7) with various amines (8A-S) using a suitable condensing reagent, followed by hydrolysis. The inhibitory effects of the resulting products on dihydrofolate reductase (DHFR), thymidylate synthetase (TS) and the growth of murine fibrosarcoma Meth A cells in culture were examined. All N5-substituted glutamine analogs (4A-S) inhibited DHFR much more strongly than TNP-351 and some analogs exhibited the same potent growth inhibition of Meth A cells as TNP-351. Some typical analogs (4Bb, 4Db, 4F, 4Oa) were also examined for inhibitory effects on the growth of methotrexate (MTX)-resistant human CCRF-CEM cells in culture and for in vivo antitumor activities against murine leukemia and solid tumors.
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