4-Isothiocyanatophenyl-a-D-mannopyranoside

4-异硫氰酸苯基-a-D-甘露糖苷,

4-Isothiocyanatophenyl alpha-D-mannopyranoside, also known as phenylisothiocyanate mannopyranoside, is a synthetic compound composed of a phenyl isothiocyanate group linked to the alpha-D-mannopyranoside sugar moiety. It was first synthesized in the 1980s as a tool for glycobiology research to study carbohydrate-protein interactions in biological processes.

Synthesis and Characterization:

The synthetic route to phenylisothiocyanate mannopyranoside involves the reaction of 4-nitrophenyl alpha-D-mannopyranoside and thiophosgene, followed by reduction with activated zinc and acid hydrolysis to give the final compound. The product is characterized by nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and high-performance liquid chromatography (HPLC).

Analytical Methods:

HPLC is commonly used to analyze the purity and stability of phenylisothiocyanate mannopyranoside and its adducts with proteins. Mass spectrometry and NMR spectroscopy are used to determine the structure and composition of the product and its derivatives.

Biological Properties:

Phenylisothiocyanate mannopyranoside has been reported to inhibit the binding of Concanavalin A (Con A), a lectin that recognizes mannose residues, to glycoproteins and glycolipids. The compound has also been shown to inhibit the attachment and entry of human immunodeficiency virus (HIV) into host cells by binding to the viral envelope glycoprotein gp120.

Toxicity and Safety in Scientific Experiments:

There are limited reports on the toxicity and safety of phenylisothiocyanate mannopyranoside in scientific experiments. However, it should be handled with care due to its reactivity to amino groups, which may lead to protein denaturation and cytotoxicity.

Applications in Scientific Experiments:

Phenylisothiocyanate mannopyranoside has been used as a tool for glycobiology research to study carbohydrate-protein interactions in biological processes. It has also been used as an antiviral agent and as a molecular probe for the identification and purification of mannose-binding proteins.

Current State of Research:

Recent studies have focused on the development of phenylisothiocyanate mannopyranoside derivatives as potential therapeutics for cancer and neurological disorders. The compound has also been used as a molecular probe for the identification and purification of mannose-binding proteins.

Potential Implications in Various Fields of Research and Industry:

Phenylisothiocyanate mannopyranoside and its derivatives have potential applications in drug discovery, particularly in the development of glycomimetic drugs that target carbohydrate-protein interactions. The compound may also have applications in the development of antiviral and anticancer drugs.

Limitations and Future Directions:

There are several limitations to the use of phenylisothiocyanate mannopyranoside, including its toxicity and reactivity with amino groups, which may limit its applicability in biological systems. Future research directions may include the development of safer and more effective derivatives, the exploration of its therapeutic potential in various disease models, and the investigation of its molecular mechanisms of action. Additionally, further research may focus on the identification and characterization of new mannose-binding proteins and the development of new glycomimetic drugs.

COA:

Name: α-D-Mannopyranosylphenyl isothiocyanate; ;4-Isothiocyanatophenyla-D-mannopyranoside   

CAS: 96345-79-8               M.F.: C₁₄H₁₅NO₆S                   M.W._: 313.33    

References:

1. Woller EK, Cloniger MJ, Biomacromolecules 2001, 2, p1052

2. Roy R, Curr. Opin. Struct. Biol. 1996, Vol6, No5, p692-702