36467-68-2 Usage
Description
N',N'',N''',N''''-Pentaacetylchitopentaose is a pentameric chito-oligosaccharide that plays a significant role in the nodulation process in leguminous plants. It is involved in the interaction between the host plant and Rhizobium bacteria, which is essential for the formation of root nodules. These nodules are crucial for the conversion of atmospheric nitrogen into ammonia, which is vital for plant growth. N',N'',N''',N''''-Pentaacetylchitopentaose is a white solid and has been shown to have anti-tumor effects.
Uses
1. Used in Plant Defense Systems:
N',N'',N''',N''''-Pentaacetylchitopentaose is used as a carbohydrate component of lipo-chitooligosaccharides secreted by Rhizobia, functioning as a signaling molecule in the host plant. This signaling molecule helps elicit plant defense systems, which is essential for the establishment of a symbiotic relationship between the plant and the bacteria.
2. Used in Nitrogen Fixation:
N',N'',N''',N''''-Pentaacetylchitopentaose is used as a substrate for Rhizobium leguminosarum nodulation protein NodL. This interaction is crucial for the formation of root nodules, which are important sites for the conversion of atmospheric nitrogen into ammonia. This process is vital for the growth and development of leguminous plants.
3. Used in Anti-Tumor Applications:
Studies have shown that N',N'',N''',N''''-Pentaacetylchitopentaose has anti-tumor effects. It is used as a potential therapeutic agent for cancer treatment, with its exact mechanism of action still being investigated.
4. Used in Immunomodulation:
N',N'',N''',N''''-Pentaacetylchitopentaose, along with chitin and chitosan, has been shown to inhibit nitric oxide production in LPS-activated RAW 264.7 macrophages. This suggests that the compound may have immunomodulatory properties, which could be useful in the development of treatments for various immune-related conditions.
Production Methods
Cell density cultivation of recombinant Escherichia coli strains harboring the nodC gene (encoding chitooligosaccharide synthase) from Azorhizobium caulinodans has been previously described as a practical method for the preparation of gram-scale quantities of penta-N-acetyl-chitopentaose. We have now extended this method to the production of allylated derivative of penta-N-acetyl-chitopentaose by using allyl 2-acetamido-2-deoxy-β-d- glucopyranoside (2) as the initial acceptor for the synthesis of target pentaoside in vivo.
Chemo-enzymatic synthesis of allyl penta-N-acetyl-chitopentaose
Huang, Gang-Liang; Zhang, Da-Wei; Zhao, Hong-Juan; Zhang, Hou-Cheng; Wang, Peng-George - Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 2042 - 2043
Check Digit Verification of cas no
The CAS Registry Mumber 36467-68-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,4,6 and 7 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 36467-68:
(7*3)+(6*6)+(5*4)+(4*6)+(3*7)+(2*6)+(1*8)=142
142 % 10 = 2
So 36467-68-2 is a valid CAS Registry Number.
36467-68-2Relevant articles and documents
Concise preparation of biologically active chitooligosaccharides
Huang
experimental part, p. 1413 - 1417 (2010/12/19)
Chitooligosaccharides (COSs) have demonstrated a diverse array of biological activities. Here we report a concise preparation method for tetra-N-acetyl-chitotetraose and penta-N-acetyl-chitopentaose. The FACE analysis showed that the partially N-acetylated COS mixture mainly contained glucosamine (GlcN) and some oligomers [(GlcN)n, n = 2-7]. The N-acetyl-D-glucosamine (GlcNAc) and peracetylated COSs [(GlcNAc)n, n = 2-7] were synthesised by treating the partially N-acetylated COS mixture with Ac2O-NaOAc. The peracetylated chitotetraose and chitopentaose were obtained by isolation of peracetylated COS mixture. NaOMe in dry MeOH was used for the deacetylation of peracetylated chitotetraose and chitopentaose, to give the tetra-N-acetyl- chitotetraose and penta-N-acetyl-chitopentaose, respectively.
