L-Glutamic acid α-tert-butyl ester is a chemically protected derivative of the naturally occurring amino acid L-Glutamic acid. In this molecule, the α-carboxyl group is esterified with a tert-butyl group to allow selective activation of the γ-carboxyl during peptide synthesis. This strategy enables controlled, stepwise peptide assembly while preventing unwanted side reactions or polymerization. The acid-labile tert-butyl group can be removed under mild acidic conditions without affecting other protecting groups or the peptide backbone, facilitating selective deprotection. This building block is crucial for synthesizing complex peptides and proteins when precise functionalization of glutamic acid is needed. It also finds use in peptidomimetic and bioactive molecule synthesis requiring selective glutamic acid modification.
Appearance
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Colorless to white crystalline solid or clear oil
Source
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Synthetically produced from L-Glutamic acid
Molecular Weight and Structure
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Molecular Weight: Approximately 217.25 g/mol
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Structure: L-Glutamic acid with the α-carboxyl protected as tert-butyl ester (-C(CH₃)₃)
Biological Activity
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No significant biological activity by itself
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Primarily a synthetic building block
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Biological activity derives from the molecules it is incorporated into
Purity and Microbial Contamination
| Parameter | Specification |
|---|---|
| Purity | Typically >98% (HPLC or GC) |
| Microbial Contamination | Not usually a concern for synthesis grade reagents |
Identity and Quality Control
| Test | Specification |
|---|---|
| NMR Spectroscopy | Confirms chemical structure and purity, including tert-butyl and glutamic acid signals |
| HPLC/GC | Determines purity and detects impurities |
| Optical Rotation | Confirms correct L-isomer stereochemistry |
| Mass Spectrometry | Confirms molecular weight |
Shelf Life and Storage
| Condition | Shelf Life |
|---|---|
| Store at 2-8°C, protected from light and moisture, under inert atmosphere (argon or nitrogen) | 1-2 years when stored properly |
Application
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Building block for peptide synthesis with selective activation of γ-carboxyl group
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Synthesis of peptidomimetics and bioactive molecules requiring specific glutamic acid functionalization
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General chemical research and development
Key Characteristics
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Protected form of L-Glutamic acid for selective reactivity
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Acid-labile tert-butyl ester on α-carboxyl group
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Enables selective peptide bond formation at γ-carboxyl
Citation
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