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Application Area

Boc-L-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-004530

CAS number

34582-32-6

Molecular Formula

C13H23NO6

Molecular Weight

289.40

IUPAC Name

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

Synonyms

Boc-L-Asp-OtBu; (S)-4-(tert-butoxy)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid

Appearance

White powder

Purity

≥ 98% (HPLC)

Density

1.139 g/cm3

Melting Point

98-112 °C

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-/m0/s1

InChI Key

RAUQRYTYJIYLTF-QMMMGPOBSA-N

Canonical SMILES

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

Boc-L-aspartic acid α-tert-butyl ester, a chemical compound commonly utilized in peptide synthesis and diverse biochemical applications, finds itself indispensable in various cutting-edge endeavors. Here are four key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a fundamental component in solid-phase peptide synthesis, Boc-L-aspartic acid α-tert-butyl ester emerges as a cornerstone in the construction of peptide chains. The Boc (tert-butyloxycarbonyl) group acts as a protective shield for the amino acid’s amine function, safeguarding it against undesirable side reactions during synthesis. After the completion of peptide chain assembly, the removal of the Boc group unveils the desired free peptide, a meticulous process crucial for the creation of complex peptides.

Drug Development: In the realm of pharmaceutical innovation, this compound plays a pivotal role in the design of peptide-based drugs and therapeutic agents. Its versatility allows for the strategic introduction of aspartic acid residues at specific locations within peptides, influencing the drug’s stability, solubility, and biological activity. This unique property is paramount in fine-tuning the pharmacokinetic and pharmacodynamic characteristics of novel drugs.

Protein Engineering: Within the domain of protein engineering research, Boc-L-aspartic acid α-tert-butyl ester proves to be a valuable asset in the precise manipulation of proteins and enzymes. By strategically incorporating aspartic acid residues at key sites, researchers can delve into the structural and functional roles of these residues, shedding light on the intricate mechanics of proteins. This methodology bears profound implications for understanding protein behavior and for crafting bespoke enzymes endowed with tailored properties.

Chemoselective Ligations: Venturing into the realm of synthetic chemistry, this compound finds its niche in facilitating chemoselective ligation strategies, a sophisticated approach aimed at uniting two functional molecules through specific, stable linkages. This precision-driven method is instrumental in constructing intricate molecular architectures with precision and efficiency. Boc-L-aspartic acid α-tert-butyl ester serves as a linchpin in the seamless execution of such ligation techniques, emerging as an indispensable tool in the arsenal of advanced chemical synthesis methodologies.

1.Efficient Fmoc/solid-phase synthesis of Abu(P)-containing peptides using Fmoc-Abu(PO3Me2)-OH.

Perich JW1. Int J Pept Protein Res. 1994 Sep;44(3):288-94.

The synthesis of the two 4-phosphono-2-aminobutanoyl-containing peptides, Leu-Arg-Arg-Val-Abu(P)-Leu-Gly-OH.CF3CO2H and Ile-Val-Pro-Asn-Abu(P)-Val-Glu-Glu-OH.CF3CO2H was accomplished by the use of Fmoc-Abu(PO3Me2)-OH in Fmoc/solid-phase peptide synthesis. The protected phosphoamino acid, Fmoc-Abu(PO3Me2)-OH, was prepared from Boc-Asp-OtBu in seven steps, the formation of the C-P linkage being effected by the treatment of Boc-Asa-OtBu with dimethyl trimethylsilyl phosphite. Peptide synthesis was performed using Wang Resin as the polymer support with both peptides assembled by the use of PyBOP for the coupling of Fmoc amino acids and 20% piperidine for cleavage of the Fmoc group from the Fmoc-peptide after each coupling cycle. Cleavage of the peptide from the resin and peptide deprotection was accomplished by the treatment of the peptide-resin with 5% thioanisole/TFA followed by cleavage of the methyl phosphonate group by 1 M bromotrimethylsilane/1 M thioanisole in TFA.

2.Synthesis of the C-terminal half of thymosin alpha 1 by the polymeric reagent method.

Mokotoff M, Patchornik A. Int J Pept Protein Res. 1983 Feb;21(2):145-54.

In this report we further show the utility and efficiency of polymer-bound 1-hydroxybenzotriazole (PHBT) as an almost ideal support for the polymeric reagent method of peptide synthesis. This was demonstrated by the synthesis of thymosin alpha 1 (15-28), in which two suitably blocked segments, Boc-Asp (OtBu)-Leu-Lys (2Cz)-Glu (OBzl)-Lys (2Cz)-Lys (2Cz)-OH (3) and Boc-Glu (OBzl)-Val-Val-Glu (OBzl)-Glu (OBzl)-Ala-Glu (OBzl)-Asn-OBzl (2), were prepared entirely by utilizing PHBT activation for each coupling step. After appropriate deblocking of 2, segments 2 and 3 were coupled by the DCC-HOBT method, followed by complete deblocking and ion-exchange chromatographic purification, affording the C-terminal half of thymosin alpha 1, H-Asp-Leu-Lys-Glu-Lys-Lys-Glu-Val-Val-Glu-Glu-Ala-Glu-Asn-OH (1).