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Application Area

Boc-D-glutamic acid α-tert-butyl ester

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

Category

BOC-Amino Acids

Catalog number

BAT-004534

CAS number

73872-71-6

Molecular Formula

C14H25NO6

Molecular Weight

303.36

IUPAC Name

(4R)-5-[(2-methylpropan-2-yl)oxy]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid

Synonyms

Boc-D-Glu-OtBu; (R)-5-(tert-Butoxy)-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid

Appearance

White powder

Purity

≥ 98% (NMR)

Density

1.121 g/cm3

Boiling Point

449.8±40.0 °C(Predicted)

Storage

Store at 2-8°C

InChI

InChI=1S/C14H25NO6/c1-13(2,3)20-11(18)9(7-8-10(16)17)15-12(19)21-14(4,5)6/h9H,7-8H2,1-6H3,(H,15,19)(H,16,17)/t9-/m1/s1

InChI Key

YMOYURYWGUWMFM-SECBINFHSA-N

Canonical SMILES

CC(C)(C)OC(=O)C(CCC(=O)O)NC(=O)OC(C)(C)C

Boc-D-glutamic acid α-tert-butyl ester, a versatile chemical compound utilized in organic chemistry and biochemistry, boasts diverse applications. Here are four key applications:

Peptide Synthesis: A cornerstone in peptide synthesis, Boc-D-glutamic acid α-tert-butyl ester serves as a protected amino acid, safeguarding against undesired reactions throughout the coupling process. The Boc protective group plays a pivotal role in orchestrating precise peptide chain assembly for research endeavors or therapeutic pursuits, facilitating the meticulous construction of peptides with finesse.

Drug Development: In the realm of pharmaceutical innovation, Boc-D-glutamic acid α-tert-butyl ester emerges as a foundational building block for peptide-based drug development. Its protective attributes enable the strategic integration of glutamic acid residues into peptide sequences, offering researchers a platform to enhance drug design for heightened efficacy and stability through comprehensive exploration of its diverse roles across distinct peptides.

Bioconjugation: An indispensable player in bioconjugation techniques, this compound assumes a central role in linking peptides to various molecules or surfaces, leveraging the ester group to streamline the conjugation process while preserving the structural integrity of peptides. The strategic application of bioconjugation methodologies utilizing Boc-D-glutamic acid α-tert-butyl ester propels the development of advanced biomedical solutions like targeted drug delivery systems.

Functional Material Synthesis: Delving into functional material synthesis, Boc-D-glutamic acid α-tert-butyl ester finds its niche in crafting innovative materials such as hydrogels and nanoparticles. Its integration into polymer matrices bestows specific characteristics, such as pH responsiveness, amplifying the utility of these materials across diverse applications like tissue engineering, where they provide a conducive environment for cell growth and differentiation, exemplifying the intersection of chemistry and materials science in cutting-edge research endeavors.

1. Amino acid-azetidine chimeras: synthesis of enantiopure 3-substituted azetidine-2-carboxylic acids

Z Sajjadi, W D Lubell J Pept Res. 2005 Feb;65(2):298-310. doi: 10.1111/j.1399-3011.2005.00228.x.

Azetidine-2-carboxylic acid (Aze) analogs possessing various heteroatomic side chains at the 3-position have been synthesized by modification of 1-9-(9-phenylfluorenyl) (PhF)-3-allyl-Aze tert-butyl ester (2S,3S)-1. 3-Allyl-Aze 1 was synthesized by regioselective allylation of alpha-tert-butyl beta-methyl N-(PhF)aspartate 13, followed by selective omega-carboxylate reduction, tosylation, and intramolecular N-alkylation. Removal of the PhF group and olefin reduction by hydrogenation followed by Fmoc protection produced nor-leucine-Aze chimera 2. Regioselective olefin hydroboration of (2S,3S)-1 produced primary alcohol 23, which was protected as a silyl ether, hydrogenated and N-protected to give 1-Fmoc-3-hydroxypropyl-Aze 26. Enantiopure (2S,3S)-3-(3-azidopropyl)-1-Fmoc-azetidine-2-carboxylic acid tert-butyl ester 3 was prepared as a Lys-Aze chimera by activation of 3-hydroxypropyl-Aze 26 as a methanesulfonate and displacement with sodium azide. Moreover, orthogonally protected azetidine dicarboxylic acid 4 was synthesized as an alpha-aminoadipate-Aze chimera by oxidation of alcohol 26. These orthogonally protected amino acid-Aze chimeras are designed to serve as tools for studying the influence of conformation on peptide activity.

2. A novel [60]fullerene amino acid for use in solid-phase peptide synthesis

F Pellarini, D Pantarotto, T Da Ros, A Giangaspero, A Tossi, M Prato Org Lett. 2001 Jun 14;3(12):1845-8. doi: 10.1021/ol015934m.

[see structure]. A fullerene derivative containing a free amino group has been condensed with N-Fmoc-L-glutamic acid alpha-tert-butyl ester to give a C60-functionalized amino acid. The carboxylic end of this amino acid has been deprotected in acidic conditions, and the resulting acid has been used for solid-phase peptide synthesis. The final peptide, cleaved from the resin, was very soluble in water solutions and showed antimicrobial activity against two representative bacteria.

3. Quinazoline antifolate thymidylate synthase inhibitors: gamma-linked L-D, D-D, and D-L dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583)

V Bavetsias, A L Jackman, R Kimbell, W Gibson, F T Boyle, G M Bisset J Med Chem. 1996 Jan 5;39(1):73-85. doi: 10.1021/jm950471+.

The syntheses of gamma-linked L-D, D-D, and D-L dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583) are described. The general methodology for the synthesis of these molecules involved the preparation of the dipeptide derivatives employing solution phase peptide synthesis followed by condensation of the dipeptide free bases with the appropriate pteroic acid analogue via diethyl cyanophosphoridate (DEPC) activation. In the final step, tert-butyl esters were removed by trifluoroacetic acid (TFA) hydrolysis. Z-L-Glu-OBut-gamma-D-Ala-OBut, for example, was prepared from alpha-tert-butyl N-(benzyloxycarbonyl)-L-glutamate and tert-butyl D-alaninate via isobutyl-mixed anhydride coupling. The Z-group was removed by catalytic hydrogenolysis and the resulting dipeptide free base condensed with 2-desamino-2-methyl-N10-propargyl-5,8-dideazapteroic acid via DEPC coupling. Finally, tert-butyl esters were removed by TFA hydrolysis to give ICI 198583-gamma-D-Ala. The compounds were tested as inhibitors of thymidylate synthase and L1210 cell growth. Good enzyme and growth inhibitory activity were found with gamma-linked L-D dipeptides, the best examples being the Glu-gamma-D-Glu derivative 35 (Ki = 0.19 nM, L1210 IC50 = 0.20 +/- 0.017 microM) and the Glu-gamma-D-alpha-aminoadipate derivative 39 (Ki = 0.12 nM, L1210 IC50 = 0.13 +/- 0.063 microM). In addition, ICI 198583 L-gamma-D-linked dipeptides were resistant to enzymatic degradation in mice.