Boc-D-alanine methyl ester
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Boc-D-alanine methyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-002703
CAS number
91103-47-8
Molecular Formula
C9H17NO4
Molecular Weight
203.24
Boc-D-alanine methyl ester
IUPAC Name
methyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Synonyms
Boc-D-Ala-Ome; (R)-Methyl 2-((tert-butoxycarbonyl)amino)propanoate
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.051g/cm3
Melting Point
34-37 °C(lit.)
Boiling Point
341.54°C (rough estimate)
Storage
Store at 2-8°C
InChI
InChI=1S/C9H17NO4/c1-6(7(11)13-5)10-8(12)14-9(2,3)4/h6H,1-5H3,(H,10,12)/t6-/m1/s1
InChI Key
GJDICGOCZGRDFM-ZCFIWIBFSA-N
Canonical SMILES
CC(C(=O)OC)NC(=O)OC(C)(C)C

Boc-D-alanine methyl ester is a chemically modified amino acid derivative used primarily in biochemical applications. Here are some key applications of Boc-D-alanine methyl ester:

Peptide Synthesis: Boc-D-alanine methyl ester is used as a building block in the synthesis of peptides and small proteins. Its Boc (tert-butyloxycarbonyl) protecting group helps in the stepwise construction of peptide chains by protecting the amine group during coupling reactions. After synthesis, the protecting group can be removed under acidic conditions, allowing the free peptide to be obtained.

Drug Development: In pharmaceutical research, Boc-D-alanine methyl ester is employed in the synthesis of peptide-based drug candidates. It aids in the production of modified peptides that can have improved pharmacokinetic and pharmacodynamic properties. By incorporating D-alanine into peptides, researchers can enhance their stability against enzymatic degradation, thereby increasing their potential as therapeutic agents.

Enzyme Inhibition Studies: Boc-D-alanine methyl ester can be used to investigate the activity of enzymes that interact with D-amino acids. By serving as a substrate or inhibitor, it helps in studying enzyme specificity and catalytic mechanisms. These insights are valuable for designing enzyme inhibitors as potential drugs for various diseases such as bacterial infections and cancer.

Proteomics: In proteomic studies, Boc-D-alanine methyl ester can be incorporated into peptides for mass spectrometry-based analysis. This allows researchers to study protein structure, function, and interactions in detail. The use of such modified peptides can enhance the detection and quantification of proteins in complex biological samples, advancing our understanding of proteomes.

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