tBuO-Ste-Glu(OtBu)-OH is a lipidated, protected glutamic acid building block frequently used in solid-phase peptide synthesis for research and development. It comprises a glutamic acid residue with both carboxylic acids protected as tert-butyl (tBu) esters, and a lipophilic stearoyl (Ste) group attached to the N-terminus via an amide bond. The tBu groups are acid-labile, permitting selective deprotection. This molecule is a key tool for synthesizing lipidated peptides with enhanced membrane permeability or solubility.
Appearance
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White to off-white solid or powder
Source
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Produced synthetically via chemical synthesis
Molecular Weight and Structure
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Molecular Weight: ~570–600 g/mol (depends on exact stereochemistry)
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Structure:
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Stearoyl (C18 saturated fatty acid) at N-terminus
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Glutamic acid (Glu) core
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Both carboxyl groups protected with tert-butyl (OtBu) esters
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Biological Activity
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No direct inherent biological activity
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Biological effect derives from incorporation into peptides or conjugates
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Stearoyl group enhances lipophilicity and membrane interaction properties
Purity and Microbial Contamination
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Purity: >95% (HPLC)
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Microbial contamination: <100 CFU/g
Identity and Quality Control
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NMR spectroscopy: Confirms structure and purity
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HPLC: Determines purity and impurities
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Mass spectrometry: Confirms molecular weight
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Optical rotation: Confirms stereochemistry (if applicable)
Shelf Life and Storage
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Shelf life: 1–2 years (properly stored)
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Storage: –20°C, protected from light and moisture
Application
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Building block in SPPS for lipidated peptide synthesis
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Used to increase solubility, stability, or membrane permeability of peptides
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Research on the impact of lipidation on peptide pharmacokinetics and activity
Key Characteristics
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Lipidated, protected glutamic acid (Stearoyl + OtBu groups)
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Acid-labile tBu protecting groups
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Enhances membrane permeability and solubility
Citation
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