氮乙酰葡萄糖胺分子结构及振动光谱相关性研究
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摘要
探究氮乙酰葡萄糖胺(N-acetyl-D-glucosamine,NAG)分子的稳定结构及其红外振动光谱之间的相关性,致力于解析出蕴含在光谱信息中的分子构象特征.研究表明,当NAG分子中乙酰胺基发生构象异构使得羰基与相邻羟基处于同一平面时,两者会产生强烈的氢键作用,形成一个螯合环,从而降低NAG分子体系的能量,并使相关羟基的红外吸收发生红移.研究结果为解析氮乙酰葡萄糖胺及其衍生物的结构与生物活性提供必要的理论基础.
The correlation between the molecular structure and vibrational spectroscopy of N-acetyl-D-glucosamine( NAG) was systematically investigated for the understanding about the conformational feature encoded in the infrared spectra. The results show that there is strong intramolecular hydrogen bond between acetamide group and its nearby hydroxyl group while they are in the same plane and form a cycle. Therefore,the potential energy of the molecule would be stabilized and the vibrational frequency of the hydroxyl group would be red shift to some extent. The results would gain insight of NAG's vibrational feature and would be helpful for understanding about the structure and biological activity of NAG and its derivatives.
The correlation between the molecular structure and vibrational spectroscopy of N-acetyl-D-glucosamine( NAG) was systematically investigated for the understanding about the conformational feature encoded in the infrared spectra. The results show that there is strong intramolecular hydrogen bond between acetamide group and its nearby hydroxyl group while they are in the same plane and form a cycle. Therefore,the potential energy of the molecule would be stabilized and the vibrational frequency of the hydroxyl group would be red shift to some extent. The results would gain insight of NAG's vibrational feature and would be helpful for understanding about the structure and biological activity of NAG and its derivatives.
引文
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[2] RODRIGUES J G,BALMAA M,MACEDO J A,et al. Glycosylation in cancer:selected roles in tumour progression,immune modulation and metastasis[J]. Cell Immunol,2018,333:46-57.
[3] LIN Z,BURNE R A. NagR differentially regulates the expression of the glm S and nag AB genes required for amino sugar me-tabolism by streptococcus mutans[J]. J Bacteriol,2015,197(22):3533-3544.
[4] BRANCA C,D'ANGELO G,CRUPI C,et al. Role of the OH and NH vibrational groups in polysaccharide-nanocompositeinteractions:a FTIR-ATR study on chitosan and chitosan/clay films[J]. Polymer,2016,99:614-622.
[5] AUBRY-ROZIER B. Role of slow-acting anti-arthritic agents in osteoarthritis(chondroitin sulfate,glucosamine,hyaluronicacid)[J]. Rev Med Suisse,2012,8(332):571-572.
[6] SERPI M,BIBBO R,ROBERTS H,et al. Novel phosphoramidate prodrugs of N-acetyl-(d)-glucosamine with antidegen-erative activity on bovine and human cartilage explants[J]. J Med Chem,2012,55(10):4629-4639.
[7] MISZKIEL A,WOJCIECHOWSKI M. Long range molecular dynamics study of interactions of the eukaryotic glucosamine-6-phosphate synthase with fructose-6-phosphate and UDP-GlcNAc[J]. J Mol Graph Model,2017,78:14-25.
[8] WANG J,ZHANG X,SUN S,et al. Online determination of quality parameters of dried soybean protein-lipid films(Fuzhu)by NIR spectroscopy combined with chemometrics[J]. J Food Meas Charact,2018,12:1473-1484.
[9] MONTEYNE T,COOPMAN R,KISHABONGO A S,et al. Analysis of protein glycation in human fingernail clippings withnear-infrared(NIR)spectroscopy as an alternative technique for the diagnosis of diabetes mellitus[J]. Clin Chem LabMed,2009,56(9):1551-1558.
[10] CHENG F F,LIANG G X,SHEN Y Y,et al. N-acetylglucosamine biofunctionalized Cd Se Te quantum dots as fluorescenceprobe for specific protein recognition[J]. Analyst,2013,138(2):666-670.
[11] SUN Z,LI C,LI L,et al. Study on feasibility of determination of glucosamine content of fermentation process using a mi-cro NIR spectrometer[J]. Spectrochim ACTA A,2018,201:153-160.
[12] GALLAS J P,GOUPIL J M,VIMONT A,et al. Quantification of water and silanol species on various silicas by couplingIR spectroscopy and in-situ thermogravimetry[J]. Langmuir,2009,25(10):5825-5834.
[13] HUANG S,YIN B,ZENG L,et al. An on-line fourier transform infrared spectrometer used for biological process measure-ment[J]. IEEE Sens J,2018,18(4):1723-1730.
[14] KOVáCS A,NYERGES B,IZVEKOV V. Vibrational analysis of N-acetyl-alpha-D-glucosamine and beta-D-glucuronic acid[J]. J Phys Chem B,2008,112(18):5728-5735.
[15] KURITA K,MATSUMURA Y,TAKAHARA H,et al. Synthesis and macrophage activation of lentinan-mimic branched a-mino polysaccharides:curdlans having N-acetyl-d-glucosamine branches[J]. Biomacromolecules,2011,12(6):2267-2274.
[16] GOCEN T,BAYARI S H,GUVEN M H. Conformational and vibrational studies of arachidonic acid,light and temperatureeffects on ATR-FTIR spectra[J]. Spectrochim ACTA A,2018,203:263-272.
[17] GHIASI R,PEIKARI A. Solvent effect on the stability and properties of platinum-substituted borirene and boryl isomers:the polarizable continuum model[J]. Russ J Phys Chem A,2016,90(11):2211-2216.
[18]欧阳顺利,张明哲,张永朝,等.三元水溶液体系中氢键作用与分子结构的拉曼光谱研究[J].高等学校化学学报,2018,39(4):758-763.
[19] VOJTA D,DOMINKOVI'CK,MILJANI'CS,et al. Intramolecular hydrogen bonding in myricetin and myricitrin. Quantumchemical calculations and vibrational spectroscopy[J]. J Mol Struct,2016,1131:242-249.
[20] LANE J R,SCHRDER S D,SAUNDERS G C,et al. Intramolecular hydrogen bonding in substituted aminoalcohols[J]. J Phys Chem A,2016,120(32):6371-6378.
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