Boc-Glycine
[CAS# 4530-20-5]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Glycine derivatives
• Name: Boc-Glycine
• Synonyms: N-(tert-Butoxycarbonyl)glycine; Boc-Gly-OH
• Molecular Formula: C₇H₁₃NO₄
• Molecular Weight: 175.18
• Protein Sequence: G
• CAS Registry Number: 4530-20-5
• EC Number: 224-864-5
• SMILES: CC(C)(C)OC(=O)NCC(=O)O

Properties

• Solubility: soluble (water), 1 mmole in 2ml CH2CL2 (Expl.)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 87-90 °C (Expl.)
• Index of Refraction: 1.609, Calc.^*
• Boiling Point: 390.6±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 190.0±23.7 °C, Calc.^*

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H318
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P305+P351+P338-P305+P354+P338-P317-P330-P337+P317-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	5	H303

• Transport Information: UN 2811

Discovery and Applications

Boc-Glycine, also known as tert-butoxycarbonyl glycine, is a protected form of the amino acid glycine widely used in peptide synthesis. Its structure features a glycine molecule bonded to a tert-butoxycarbonyl (Boc) protecting group on the amino functionality. The Boc group shields the amino group during synthesis, allowing for selective reactivity of the carboxyl group, thus enabling the stepwise formation of peptides. The introduction of Boc-Glycine marked an important milestone in organic chemistry, particularly in the field of solid-phase peptide synthesis (SPPS), where Boc-protected amino acids were initially favored due to their compatibility with the method.

Boc-Glycine’s primary application lies in peptide synthesis, where it is often the starting material or an intermediate for constructing larger peptides and proteins. During synthesis, the Boc group serves as a removable protecting group for the amino function, easily cleaved under acidic conditions without affecting other parts of the molecule. This selective deprotection allows chemists to incorporate Boc-Glycine into multi-step syntheses without unwanted side reactions, facilitating the assembly of complex peptide chains. It also allows for the customization of peptides for specific biological activities, making it crucial for developing new therapeutic agents, research reagents, and diagnostic tools.

In addition to peptide synthesis, Boc-Glycine finds utility in drug discovery and biochemical research. Its protected structure is useful for synthesizing modified glycine derivatives and other amino acid conjugates for structure-activity studies in drug design. In medicinal chemistry, for example, Boc-Glycine is often incorporated into larger molecules that serve as enzyme inhibitors, receptor agonists, or antagonists, providing researchers with versatile tools for understanding and modulating biological processes. Furthermore, the use of Boc-protected amino acids, including Boc-Glycine, has extended into polymer chemistry, where they are incorporated into biodegradable polymers for biomedical applications.

References

2024. Design, synthesis, and mechanism study of novel tetrahydroisoquinoline derivatives as antifungal agents. Molecular Diversity.
DOI: 10.1007/s11030-024-11012-6

2023. Alkyl-Indole Derivatives of Unnatural Tetrapeptides: Synthesis and Evaluation of Biological Activity. Moscow University Chemistry Bulletin, 78(2).
DOI: 10.3103/s0027131423020086

2022. Nano-CeO2-loaded chitosan-bocglycine zinc complex for the photocatalytic degradation of picric acid by the combination of Fenton’s reagent. Applied Physics A, 128(9).
DOI: 10.1007/s00339-022-05841-1