What Is Glycine Ethyl Ester Hydrochloride and How Is It Used in Peptide Synthesis?
Technical Introduction
Glycine Ethyl Ester Hydrochloride is a white to off-white crystalline powder that serves as a protected form of the simplest amino acid, glycine. Its structure consists of glycine in which the carboxylic acid group has been esterified with ethanol, and it exists as the hydrochloride salt to enhance stability, purity, and handling.
This derivative is widely applied in organic synthesis, peptide manufacturing, and pharmaceutical intermediates, where ester protection facilitates selective reactions and efficient coupling.
Applications
1. Peptide Synthesis
Acts as a protected glycine building block, preventing unwanted side reactions at the carboxyl group.
Facilitates amide bond formation with activated carboxylic acids.
Improves yields and reduces purification steps in solid-phase peptide synthesis (SPPS).
2. Pharmaceutical Intermediates
Used to prepare bioactive glycine derivatives for drugs, nutraceuticals, and research chemicals.
Serves as a precursor in prodrug synthesis, where the ester group can be hydrolyzed in vivo.
3. Organic Synthesis
Functions as a reactive intermediate in the preparation of fine chemicals.
Useful in asymmetric synthesis for chiral molecule construction.
Advantages
High Reactivity: Ester form enhances nucleophilic attack on activated carboxyl groups.
Improved Purity: Hydrochloride salt minimizes impurities during storage.
Stable Handling: Solid crystalline form is easier to weigh and transport.
Versatile Usage: Applicable in both lab-scale and industrial synthesis.
Typical Parameters
| Property | Value |
|---|---|
| Chemical Formula | C₄H₁₀ClNO₂ |
| Molecular Weight | 139.58 g/mol |
| CAS Number | 623-33-6 |
| Appearance | White to off-white crystalline powder |
| Purity (%) | ≥98.0 |
| Melting Point (°C) | 147–151 |
| Solubility | Soluble in water, ethanol, methanol |
| Storage | Store in a cool, dry place, tightly sealed |
| Shelf Life | 24 months (sealed) |
FAQs
Q1: Why use the hydrochloride salt form instead of the free base?
A1: The hydrochloride form is more stable, less hygroscopic, and easier to store without degradation.
Q2: Can it be directly used in aqueous reactions?
A2: Yes, it dissolves readily in water and polar solvents.
Q3: How is the ester group removed after synthesis?
A3: Through acid or base hydrolysis, regenerating the free carboxylic acid group of glycine.
Q4: Is it suitable for large-scale peptide production?
A4: Yes, it is widely used in industrial peptide synthesis due to its stability and reactivity.
Q5: What safety precautions are required?
A5: Handle with gloves and eye protection; avoid inhalation and prolonged skin contact.
Free Consultation
Name*
E-Mail*
TEL
Message*