Boc-L-aspartic acid β-cyclohexyl ester
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Boc-L-aspartic acid β-cyclohexyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-004531
CAS number
73821-95-1
Molecular Formula
C15H25NO6
Molecular Weight
315.40
Boc-L-aspartic acid β-cyclohexyl ester
IUPAC Name
(2S)-4-cyclohexyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid
Synonyms
Boc-L-Asp(OcHex)-OH
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.18±0.1 g/cm3(Predicted)
Melting Point
88-102 °C
Boiling Point
487.2±40.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C15H25NO6/c1-15(2,3)22-14(20)16-11(13(18)19)9-12(17)21-10-7-5-4-6-8-10/h10-11H,4-9H2,1-3H3,(H,16,20)(H,18,19)/t11-/m0/s1
InChI Key
NLPQIWFEEKQBBN-NSHDSACASA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC(=O)OC1CCCCC1)C(=O)O

Boc-L-aspartic acid β-cyclohexyl ester is a chemical compound used in various bioscience applications, particularly in peptide synthesis and drug development. Here are some key applications of Boc-L-aspartic acid β-cyclohexyl ester:

Peptide Synthesis: Boc-L-aspartic acid β-cyclohexyl ester is commonly used as a protected amino acid in the solid-phase synthesis of peptides. The Boc (tert-butyloxycarbonyl) protecting group stabilizes the amino acids during the synthesis process, preventing unwanted side reactions. By using this compound, researchers can efficiently build complex peptide sequences with high fidelity.

Drug Development: During the early phases of drug discovery, Boc-L-aspartic acid β-cyclohexyl ester can be utilized for the design and synthesis of peptide-based drug candidates. Protecting groups like Boc ensure the structural integrity of the peptides, which are often screened for biological activity. This methodology supports the development of novel therapeutics targeting a wide range of conditions, from infectious diseases to cancer.

Protein Engineering: Researchers use Boc-L-aspartic acid β-cyclohexyl ester in protein engineering to introduce specific modifications in proteins. By strategically incorporating such modified amino acids, scientists can explore protein structure-function relationships and design proteins with enhanced or novel functionalities. This is critical for advancements in enzyme engineering and the creation of biocatalysts.

Biomaterials Development: Boc-L-aspartic acid β-cyclohexyl ester plays a role in the development of biomaterials, such as peptide-based hydrogels or scaffolds. These materials are used in tissue engineering and regenerative medicine due to their biocompatibility and ability to mimic the natural extracellular matrix. The modified peptides can lend unique properties to the biomaterials, improving their mechanical and biological performance.

1.Synthesis of beta- and gamma-fluorenylmethyl esters of respectively N alpha-Boc-L-aspartic acid and N alpha-Boc-L-glutamic acid.
al-Obeidi F1, Sanderson DG, Hruby VJ. Int J Pept Protein Res. 1990 Mar;35(3):215-8.
The orthogonal synthesis of N alpha-Boc-L-aspartic acid-gamma-fluorenylmethyl ester and N alpha-Boc-L-glutamic acid-delta-fluorenylmethyl ester is reported. This is a four-step synthesis that relies on the selective esterification of the side-chain carboxyl groups on N alpha-CBZ-L-aspartic acid and N alpha-CBZ-L-glutamic acid. Such selectivity is accomplished by initially protecting the alpha-carboxyl group through the formation of the corresponding 5-oxo-4-oxazolidinone ring. Following side-chain esterification, the alpha-carboxyl and alpha-amino groups are deprotected with acidolysis. Finally, the alpha-amino group is reprotected with the t-butyl-oxycarbonyl (Boc) group. Thus aspartic acid and glutamic acid have their side-chain carboxyl groups protected with the base-labile fluorenylmethyl ester (OFm) and their alpha-amino groups protected with the acid-labile Boc group. These residues, when used in conjunction with N alpha-Boc-N epsilon-Fmoc-L-lysine, are important in the formation of side-chain to side-chain cyclizations, via an amide bridge, during solid-phase peptide synthesis.
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