Fmoc-L-aspartic acid β-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino]benzyl ester
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Fmoc-L-aspartic acid β-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino]benzyl ester

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

The Dmab group can be cleaved selectively in the presence of tBu-based protected groups by treatment with 2% hydrazine in DMF, making this derivative an extremely useful tool for the preparation of cyclic peptides by FMOC SPPS.

Category
Fmoc-Amino Acids
Catalog number
BAT-003742
CAS number
269066-08-2
Molecular Formula
C39H42N2O8
Molecular Weight
666.70
Fmoc-L-aspartic acid β-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino]benzyl ester
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[[4-[[1-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)-3-methylbutylidene]amino]phenyl]methoxy]-4-oxobutanoic acid
Synonyms
Fmoc-L-Asp(ODmab)-OH; Fmoc-Asp(ODmab)-OH; N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-aspartic acid 4-[[4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]phenyl]methyl] ester
Appearance
White to yellow powder or off-white powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.264±0.06 g/cm3
Melting Point
142-147 °C
Boiling Point
841.0±65.0 °C
Storage
Store at -20 °C
InChI
InChI=1S/C39H42N2O8/c1-23(2)17-31(36-33(42)19-39(3,4)20-34(36)43)40-25-15-13-24(14-16-25)21-48-35(44)18-32(37(45)46)41-38(47)49-22-30-28-11-7-5-9-26(28)27-10-6-8-12-29(27)30/h5-16,23,30,32,40H,17-22H2,1-4H3,(H,41,47)(H,45,46)/t32-/m0/s1
InChI Key
FLMMHDDOOIGEPG-YTTGMZPUSA-N
Canonical SMILES
CC(C)CC(=C1C(=O)CC(CC1=O)(C)C)NC2=CC=C(C=C2)COC(=O)CC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

Fmoc-L-aspartic acid β-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino]benzyl ester is a specialized chemical compound used predominantly in peptide synthesis and drug development. This compound is an ester derivative of aspartic acid, which is a naturally occurring amino acid. It features a fluorenylmethoxycarbonyl (Fmoc) group, a common protecting group in peptide chemistry, which is used to protect the amino group during synthesis. The β-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino]benzyl ester structure is specifically designed to enhance the stability and reactivity of the peptide chain during synthetic processes. This makes it a valuable tool in the creation of complex peptide sequences and pharmaceutical compounds.

One key industrial application of Fmoc-L-aspartic acid β-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino]benzyl ester is in the pharmaceutical industry for drug development. The compound's role in peptide synthesis facilitates the production of peptides with high purity and specific biological activities, which are crucial for developing new therapeutic agents. By allowing precise control over peptide chain assembly, it supports the creation of novel drugs targeting various diseases.

In the field of biotechnology, this compound is used to synthesize bioactive peptides that can be utilized in diagnostic assays and research tools. The high stability and reactivity provided by the Fmoc protection group are essential for constructing peptides that are used in assays to detect biological markers or in the development of new diagnostic methods. This application helps in advancing medical research and improving diagnostic capabilities.

Fmoc-L-aspartic acid β-4-[N-{1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl}amino]benzyl ester also plays a role in materials science, particularly in the development of functionalized materials and polymers. The compound's ability to form stable peptide bonds can be utilized to create advanced materials with specific properties, such as enhanced mechanical strength or tailored chemical reactivity. These materials have applications in various sectors, including electronics and manufacturing.

Finally, in the field of chemical synthesis, this compound is used to develop new catalysts and reagents. Its chemical structure allows it to participate in diverse reactions, making it a useful component in the design of novel catalytic systems. These systems are crucial for improving the efficiency and selectivity of chemical processes across different industrial applications.

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