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Application Area

Boc-D-aspartic 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-004524

CAS number

77004-75-2

Molecular Formula

C13H23NO6

Molecular Weight

289.40

IUPAC Name

(3R)-4-[(2-methylpropan-2-yl)oxy]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid

Synonyms

Boc-D-Asp-OtBu; (R)-4-(tert-butoxy)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid

Appearance

White powder

Purity

≥ 98% (NMR)

Density

1.139 g/cm3

Boiling Point

429.0±40.0 °C(Predicted)

Storage

Store at 2-8°C

InChI

InChI=1S/C13H23NO6/c1-12(2,3)19-10(17)8(7-9(15)16)14-11(18)20-13(4,5)6/h8H,7H2,1-6H3,(H,14,18)(H,15,16)/t8-/m1/s1

InChI Key

RAUQRYTYJIYLTF-MRVPVSSYSA-N

Canonical SMILES

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

Boc-D-aspartic acid α-tert-butyl ester, a pivotal intermediate in synthetic organic chemistry, finds diverse applications in peptide synthesis and beyond. Here, we explore four key applications presented with high perplexity and burstiness:

Peptide Synthesis: Acting as a cornerstone in peptide synthesis, Boc-D-aspartic acid α-tert-butyl ester serves as a crucial building block in the solid-phase assembly of peptides. Its robust protecting groups enable the methodical construction of peptide chains, warding off unwanted side reactions. This compound plays an instrumental role in crafting peptides for both research and therapeutic endeavors, underlining its significance in the realm of biomolecular synthesis.

Drug Development: Within the realm of pharmaceutical research, this compound integrates seamlessly into peptide-based drug candidates, facilitating the exploration of their biological functions and stability. The inclusion of the Boc group shields the aspartic acid residue during chemical transformations, ensuring its structural integrity. By expediting the synthesis of peptide-based drugs through the provision of a stable precursor, this compound propels advancements in drug development and delivery.

Enzyme Inhibitor Design: Unlocking the potential for tailored enzyme modulation, Boc-D-aspartic acid α-tert-butyl ester emerges as a potent tool for designing and formulating inhibitors that selectively target specific enzymes. These inhibitors emulate natural substrates, effectively obstructing enzyme activity and serving as therapeutic interventions. This strategic approach is instrumental in fostering the creation of treatments aimed at combatting diseases rooted in enzyme dysfunction, marking a pivotal advancement in medicinal chemistry.

Bioconjugation: In the domain of bioconjugation methodologies, this compound plays a vital role in facilitating the attachment of peptides and other biomolecules onto diverse substrates. The adaptability of the ester group allows for facile modifications, enabling the introduction of functional groups for conjugation purposes. This application not only enhances the exploration of protein interactions but also propels the development of precision-targeted drug delivery systems, reshaping the landscape of bioconjugation techniques.

1.Potent and fully noncompetitive peptidomimetic inhibitor of multidrug resistance P-glycoprotein.

Arnaud O1, Koubeissi A, Ettouati L, Terreux R, Alamé G, Grenot C, Dumontet C, Di Pietro A, Paris J, Falson P. J Med Chem. 2010 Sep 23;53(18):6720-9. doi: 10.1021/jm100839w.

N(α)-Boc-l-Asp(OBn)-l-Lys(Z)-OtBu (reversin 121, 1), an inhibitor of the P-gp ABC transporter, was used to conceive compounds inhibiting the drug efflux occurring through the Hoechst 33342 and daunorubicin transport sites of P-gp, respectively H and R sites. Replacement of the aspartyl residue by trans-4-hydroxy-l-proline (4(R)Hyp) gave compounds 11 and 15 characterized by half-maximal inhibitory concentrations (IC(50)) of 0.6 and 0.2 μM, which are 2- and 7-fold lower than that of the parent molecule. The difference in IC(50) between 11 and 15 rests on the carbonyl group of the peptidyl bond, reduced in 15. Those compounds are rather specific of P-gp, having no or limited activity on MRP1 and BCRP. 15 displayed no marked cytotoxicity up to 10-fold its IC(50). Importantly, 15 equally inhibited the Hoechst 33342 and daunorubicin effluxes through a typical noncompetitive inhibition mechanism, suggesting its binding to a site different from the H and R drug-transport sites.

2.Synthesis and structure-activity relationships of a novel antifungal agent, azoxybacilin.

Ohwada J1, Umeda I, Ontsuka H, Aoki Y, Shimma N. Chem Pharm Bull (Tokyo). 1994 Aug;42(8):1703-5.

A new antifungal substance, azoxybacilin (an unusual amino acid with an azoxy moiety) and its derivatives have been synthesized from Boc-L-Asp-OtBu utilizing the Moss procedure for the preparation of the azoxy moiety. The ester derivative, Ro 09-1824, showed more potent antifungal activity and a broader antifungal spectrum than azoxybacilin did.

3.Solid-Phase Total Synthesis of Bacitracin A.

Lee J1, Griffin JH, Nicas TI. J Org Chem. 1996 Jun 14;61(12):3983-3986.

An efficient solid-phase method for the total synthesis of bacitracin A is reported. This work was undertaken in order to provide a general means of probing the intriguing mode of action of the bacitracins and exploring their potential for use against emerging drug-resistant pathogens. The synthetic approach to bacitracin A involves three key features: (1) linkage to the solid support through the side chain of the L-asparaginyl residue at position 12 (L-Asn(12)), (2) cyclization through amide bond formation between the alpha-carboxyl of L-Asn(12) and the side chain amino group of L-Lys(8), and (3) postcyclization addition of the N-terminal thiazoline dipeptide as a single unit. To initiate the synthesis, Fmoc L-Asp(OH)-OAllyl was attached to a PAL resin. The chain of bacitracin A was elaborated in the C-to-N direction by sequential piperidine deprotection/HBTU-mediated coupling cycles with Fmoc D-Asp(OtBu)-OH, Fmoc L-His(Trt)-OH, Fmoc D-Phe-OH, Fmoc L-Ile-OH, Fmoc D-Orn(Boc)-OH, Fmoc L-Lys(Aloc)-OH, Fmoc L-Ile-OH, Fmoc D-Glu(OtBu)-OH, and Fmoc L-Leu-OH.