Bicine
[CAS# 150-25-4]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Glycine derivatives
• Name: Bicine
• Synonyms: Diethylolglycine; N,N-Bis(2-hydroxyethyl)glycine
• Molecular Formula: C₆H₁₃NO₄
• Molecular Weight: 163.17
• Protein Sequence: G
• CAS Registry Number: 150-25-4
• EC Number: 205-755-1
• SMILES: C(CO)N(CCO)CC(=O)O

Properties

• Solubility: 1 M (water 20 °C)
• Melting point: 190-192 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

N,N-Bis(2-hydroxyethyl)glycine, part of the Good family of buffers, was developed by Dr. Norman Good and his colleagues in the 1960s. These buffers were specifically designed to meet the requirements of biological and biochemical research, providing a stable pH environment. The synthesis of N,N-Bis(2-hydroxyethyl)glycine provides effective buffering in the pH range near neutrality, which is essential for many biochemical processes.

The molecular formula of N,N-Bis(2-hydroxyethyl)glycine is C6H13NO4. Structurally, it consists of a glycine molecule with two hydroxyethyl groups attached to the nitrogen atom of the molecule, which enhances its solubility and buffering capacity. N,N-Bis(2-hydroxyethyl)glycine is a zwitterionic compound, which means that it contains both positive and negative charges, which contributes to its stability as a buffer. It has a pKa of 8.3 at 25°C, making it suitable for buffering in the pH range of 7.6 to 9.0.

N,N-Bis(2-hydroxyethyl)glycine is widely used as a buffer in a variety of biochemical and molecular biology experiments. Its stability and compatibility with a range of biomolecules make it ideal for maintaining pH in enzymatic reactions, nucleic acid purification, and protein assays. It is particularly useful in applications that require a stable pH close to neutral.

In electrophoresis, N,N-Bis(2-hydroxyethyl)glycine is used to prepare buffer solutions that maintain a stable pH during protein and nucleic acid separations. For example, in Tris-Bicine-EDTA (TBE) buffer, N,N-Bis(2-hydroxyethyl)glycine helps ensure consistent migration of DNA and RNA, allowing accurate analysis of their size and conformation.

N,N-Bis(2-hydroxyethyl)glycine is used in protein purification protocols such as ion exchange chromatography and affinity chromatography. Its buffering capacity helps maintain the pH of the solution, ensuring that proteins remain in their native functional state during purification. This stability is essential for maintaining protein activity and integrity.

In cell culture applications, N,N-Bis(2-hydroxyethyl)glycine helps maintain the pH of the culture medium, providing a stable environment for cell growth and function. This stability is critical for sensitive cell lines and primary cultures, which require precise pH control for optimal growth and differentiation.

N,N-Bis(2-hydroxyethyl)glycine is an important component in diagnostic reagent formulations, especially those that require a stable pH. Its non-toxic nature and compatibility with a variety of biological systems make it suitable for diagnostic assays and kits.

References

2021. Substitution of histidine 30 by asparagine in manganese superoxide dismutase alters biophysical properties and supports proliferation in a K562 leukemia cell line. European biophysics journal : EBJ, 50(3).
DOI: 10.1007/s00249-021-01544-2

2007. Ribulose-1,5-bisphosphate carboxylase/oxygenase from thermophilic cyanobacterium Thermosynechococcus elongatus. Photosynthesis Research, 94(2).
DOI: 10.1007/s11120-007-9240-7

1979. Glycoprotein galactosyltransferase activity in synaptic junctional complexes isolated from rat forebrain. Neurochemical Research, 4(3).
DOI: 10.1007/bf00963803