104371-51-9 , Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-a-D-muramic acid methyl ester,
苄基-2-乙酰氨基-2-脱氧-4,6-O-苄叉-a-D-胞壁酸甲酯,
CAS:104371-51-9
C26H31NO8 / 485.53
MFCD03425499
苄基-2-乙酰氨基-2-脱氧-4,6-O-苄叉-a-D-胞壁酸甲酯,
Benzyl N-Acetyl-4,6-O-benzylidene-alpha-D-muramic Acid Methyl Ester (Bn-MurNAc) is a synthetic form of a natural bacterial cell wall component, MurNAc. This molecule has been widely used in scientific research due to its unique chemical and biological properties, as well as its potential applications in various fields of research and industry.
Definition and Background:
MurNAc is a key component of bacterial cell walls, along with N-acetylglucosamine (GlcNAc), which plays a critical role in maintaining bacterial cell shape and stability. Bn-MurNAc is a synthetic form of MurNAc that has been modified by the addition of a benzylidene group at the C4 and C6 positions of the GlcNAc moiety.
Synthesis and Characterization:
Bn-MurNAc can be synthesized through a multistep process starting from GlcNAc. The benzylidene group is introduced using benzaldehyde and the protecting groups are selectively removed using specific reagents. The final product can be purified through various chromatography techniques. The synthesized Bn-MurNAc is characterized by various spectroscopic techniques such as NMR and mass spectrometry.
Analytical Methods:
Bn-MurNAc can be analyzed using various analytical techniques such as high-performance liquid chromatography (HPLC), gas chromatography (GC), and capillary electrophoresis (CE). These methods can be used to analyze the purity, identity, and quantity of Bn-MurNAc in various samples.
Biological Properties:
Bn-MurNAc has been shown to have various biological properties, including being a substrate for bacterial cell wall biosynthesis, an inhibitor of bacterial enzymes, and a modulator of the immune response. It has also been shown to promote cell adhesion and cell proliferation in various cell types.
Toxicity and Safety in Scientific Experiments:
Bn-MurNAc has been shown to be non-toxic and safe in scientific experiments, with no reported adverse effects or toxicity in animal studies. However, as with any chemical, proper safety measures and precautions should be taken when handling Bn-MurNAc.
Applications in Scientific Experiments:
Bn-MurNAc has been used extensively in scientific research, particularly in the fields of bacterial cell wall biosynthesis, immunology, and cell biology. It has been used as a substrate for bacterial enzymes, a tool for investigating the immune response, and a modulator of cell adhesion and proliferation.
Current State of Research:
The current state of research on Bn-MurNAc is focused on its potential applications in various fields of research and industry. Recent studies have investigated its use as a therapeutic agent for bacterial infections, its role in promoting wound healing, and its potential as a biomaterial for tissue engineering.
Potential Implications in Various Fields of Research and Industry:
Bn-MurNAc has potential implications in various fields of research and industry, including bacterial infection treatment, immunotherapy, wound healing, and tissue engineering. Its unique properties make it a promising candidate for further research and development in these fields.
Limitations and Future Directions:
One limitation of Bn-MurNAc is its limited solubility in aqueous solutions, which can affect its applicability in certain scientific experiments. Future research could focus on developing new formulations or delivery methods to overcome this limitation. Other future directions include investigating its potential applications in cancer research and drug delivery.
In conclusion, Bn-MurNAc is a synthetic form of a natural bacterial cell wall component that has been widely used in scientific research due to its unique properties and potential applications in various fields of research and industry. Its safety, non-toxicity, and numerous applications make it a promising candidate for further research and development in the future.
CAS Number | 104371-51-9 |
Product Name | Benzyl N-Acetyl-4,6-O-benzylidene-alpha-D-muramic Acid Methyl Ester |
IUPAC Name | methyl (2R)-2-[[(6S,7S,8R,8aS)-7-acetamido-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propanoate |
Molecular Formula | C₂₆H₃₁NO₈ |
Molecular Weight | 485.53 |
InChI | InChI=1S/C26H31NO8/c1-16(24(29)30-3)33-23-21(27-17(2)28)26(31-14-18-10-6-4-7-11-18)34-20-15-32-25(35-22(20)23)19-12-8-5-9-13-19/h4-13,16,20-23,25-26H,14-15H2,1-3H3,(H,27,28)/t16-,20?,21+,22-,23-,25?,26+/m1/s1 |
SMILES | CC(C(=O)OC)OC1C(C(OC2C1OC(OC2)C3=CC=CC=C3)OCC4=CC=CC=C4)NC(=O)C |
Synonyms | N-Acetyl-1-O-(phenylmethyl)-4,6-O-(phenylmethylene)-α-muramic Acid Methyl Ester; [3(R)]-Phenylmethyl 2-(Acetylamino)-2-deoxy-3-O-(2-methoxy-1-methyl-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-glucopyranoside; |
CAS No: 104371-51-9 MDL No: MFCD03425499 Chemical Formula: C26H31NO8 Molecular Weight: 485.53 |
References: 1. J. Biol. Chem., 1952, 194, p8852. Ann. NY Acad. Sci., 1974, 235, p293. J. Am. Chem. Soc., 1963, 28, p2983 |
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