N-α-(t-Butoxycarbonyl)-N-α-methyl-L-aspartic acid β-t-butyl ester
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N-α-(t-Butoxycarbonyl)-N-α-methyl-L-aspartic acid β-t-butyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-001275
CAS number
957208-71-8
Molecular Formula
C14H25NO6
Molecular Weight
303.35
IUPAC Name
2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
Synonyms
N-alpha-(t-Butoxycarbonyl)-N-alpha-methyl-L-aspartic acid beta-t-butyl ester; Boc-MeAsp(OtBu)-OH
InChI
InChI=1S/C14H25NO6/c1-13(2,3)20-10(16)8-9(11(17)18)15(7)12(19)21-14(4,5)6/h9H,8H2,1-7H3,(H,17,18)
InChI Key
NXCHYNDSEYTLJK-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)CC(C(=O)O)N(C)C(=O)OC(C)(C)C

N-α-(t-Butoxycarbonyl)-N-α-methyl-L-aspartic acid β-t-butyl ester, commonly abbreviated as Boc-Asp(OMe)-OtBu, is an essential derivative in the field of peptide chemistry. It is a protected form of aspartic acid, where both the α-amino and β-carboxyl groups are masked by t-butoxycarbonyl (Boc) and t-butyl ester (OtBu) groups, respectively. These protecting groups prevent unwanted reactions during synthesis processes, making it a crucial intermediate for the stepwise assembly of peptides. The compound is especially valued for its stability and ease of deprotection, facilitating precise and efficient peptide synthesis.

In pharmaceutical development, N-α-(t-Butoxycarbonyl)-N-α-methyl-L-aspartic acid β-t-butyl ester is widely used for the production of active pharmaceutical ingredients (APIs). Its role as a protected amino acid enables the construction of complex peptide drugs with high specificity. Pharmaceutical companies leverage its ability to contribute to controlled synthesis, leading to the creation of highly purified peptides that are critical in various therapeutic areas such as oncology and metabolic disorders.

Another major application of this compound is in the creation of peptide-based diagnostic agents. Peptide sequences with specific biological recognition sites are often required for diagnostic tests and imaging techniques. Boc-Asp(OMe)-OtBu plays a key role in the synthesis of these peptides, providing the necessary building blocks while protecting the functional groups that might otherwise interfere with the assembly of the diagnostic molecule. This ensures accurate and reliable results in diagnostic applications.

In the field of biotechnology, this compound is employed for the preparation of biomaterials used in tissue engineering and regenerative medicine. Peptide-based scaffolds, which promote cell growth and tissue regeneration, require precise peptide sequences to function effectively. The use of N-α-(t-Butoxycarbonyl)-N-α-methyl-L-aspartic acid β-t-butyl ester allows for the controlled synthesis of these sequences, contributing to the development of advanced biomaterials.

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