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Application Area

Fmoc-D-aspartic acid β-tert-butyl ester

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

Category

Fmoc-Amino Acids

Catalog number

BAT-003635

CAS number

112883-39-3

Molecular Formula

C23H25NO6

Molecular Weight

411.50

IUPAC Name

(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid

Synonyms

Fmoc-D-Asp(OtBu)-OH; (R)-2-((((9H-FLUOREN-9-YL)METHOXY)CARBONYL)AMINO)-4-(TERT-BUTOXY)-4-OXOBUTANOIC ACID

Appearance

White powder

Purity

≥ 99.8% (Chiral HPLC)

Density

1.251±0.06 g/cm3(Predicted)

Melting Point

145-160 °C

Boiling Point

620.8±55.0 °C(Predicted)

Storage

Store at 2-8 °C

InChI

InChI=1S/C23H25NO6/c1-23(2,3)30-20(25)12-19(21(26)27)24-22(28)29-13-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,24,28)(H,26,27)/t19-/m1/s1

InChI Key

FODJWPHPWBKDON-LJQANCHMSA-N

Canonical SMILES

CC(C)(C)OC(=O)CC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-D-aspartic acid β-tert-butyl ester, a key player in peptide synthesis, finds its applications in various domains. Here are four noteworthy applications:

Peptide Synthesis: An integral component of solid-phase peptide synthesis, Fmoc-D-aspartic acid β-tert-butyl ester facilitates the construction of intricate peptides and proteins. Its unique ability to integrate D-amino acids into peptides can modify the biological activity or stability of the final molecules. Leveraging an orthogonal protecting group strategy, this compound is ideal for the gradual assembly of peptides, allowing for meticulous customization in peptide design.

Pharmaceutical Development: In the realm of drug discovery, Fmoc-D-aspartic acid β-tert-butyl ester plays a crucial role in crafting peptides with therapeutic potential. The incorporation of D-amino acids, such as this compound, aids in the creation of peptide drugs that are more resilient to enzymatic breakdown. This breakthrough translates into extended and heightened efficacy in treating a multitude of diseases.

Protein Engineering: Pioneering researchers harness Fmoc-D-aspartic acid β-tert-butyl ester to engineer proteins with tailored properties and functions. By integrating D-amino acids, scientists can engineer proteins with heightened stability and resistance to enzymatic cleavage. This innovation holds particular significance in biotechnological applications where protein longevity and activity are paramount, showcasing the transformative power of protein engineering.

Biomaterial Development: Beyond peptide synthesis and drug discovery, this compound finds its place in the realm of biomaterial development, notably in the creation of hydrogels and scaffolds for tissue engineering and regenerative medicine. The incorporation of D-amino acids enhances the mechanical strength and durability of these biomaterials, rendering them more resistant to biodegradation. This enhancement elevates the performance and longevity of biomedical materials, setting new standards for clinical applications in tissue engineering and regenerative medicine.

2. Antiapoptotic effect of benzyloxycarbonyl-aspartyl-(beta-tertier-butyl ester)-bromomethylketone (Z-D(OtBu)-Bmk), an intermediate of interleukin-1 beta converting enzyme inhibitors

K Németh, G Bugovics, J I Székely Int J Immunopharmacol. 1997 Apr;19(4):215-25. doi: 10.1016/s0192-0561(97)00026-x.

The effect of several interleukin-1 beta converting enzyme (ICE) inhibitors on apoptosis was examined. The ICE inhibitors tested were peptide aldehydes such as ethyloxycarbonyl-Ala-Tyr-Val-Ala-Asp-aldehyde (Etoco-AYVAD-CHO), acetyl-Tyr-Val-Ala-Asp-aldehyde (Ac-YVAD-CHO), benzyloxycarbonyl-Val-His-Asp-aldehyde (Z-VHD-CHO), a tetrapeptide chloromethylketone, acetyl-Tyr-Val-Ala-Asp-chloromethylketone (Ac-YVAD-Cmk) and their common intermediate benzyloxycarbonyl-Asp-(beta-tertier-butyl ester)-bromomethylketone (Z-D(OtBu)-Bmk). Apoptosis was induced with several chemical agents conventionally used for this purpose in THP-1, L929, NB-41A3 cell lines and mouse thymocytes. DNA fragmentation during apoptosis was measured by conventional gel electrophoresis and ELISA. The cell morphology was examined by hematoxylin/eosin staining method. Cell viability was also monitored by MTT assay. Contrary to expectations, the peptide aldehydes listed above and Ac-YVAD-Cmk, known as highly specific ICE inhibitors, did not inhibit the apoptosis of these cell types. However, Z-D(OtBu)-Bmk, which had no relevant inhibitory activity on ICE, potently blocked the DNA fragmentation in THP-1 cells and thymocytes whichever of the inducing agents was used. In the other two cell lines Z-D(OtBu)-Bmk was inactive. The apoptotic cell morphology was also inhibited by Z-D(OtBu)-Bmk. Nevertheless, Z-D(OtBu)-Bmk failed to prevent the loss of mitochondrial activity and the cell destruction in the late phase of apoptosis. These data suggest that ICE is not involved in the apoptotic cell death induced by chemical agents. Thus, Z-D(OtBu)-Bmk, a common intermediate of some ICE inhibitors, may be a useful antiapoptotic agent for studying the early events of apoptosis in some cell types.