纤维素前驱物6-13C标记示踪研究纤维素与木质素连接方式

doi:10.3969/j.issn.0253-2417.2014.01.007

Abstract

Abstract: In this paper, carbohydrate part of the lignin-carbohydrate complexes(LCC) in cell wall was labelled with ¹³C and traced with ¹³C NMR. Cellulose precursor, i.e., uridine diphoshphate glucose-[6-¹³C], was synthesized, and injected into a living ginkgo tree together with lignin inhibitor AOPP and exogenous lignin precursor. It is proved that uridine diphoshphate glucose-[6-¹³C] is a suitable precursor for selective ¹³C-enrichment of cellulose in a plant. The specifically ¹³C-enriched LCC was isolated from the newly formed xylem of ginkgo shoots. Then it was degraded by cellulase and hemicellulase. Thus the lignin-rich fractions,which were called enzyme-degraded LCC (EDLCC), were obtained. By determining their FT-IR and ¹³C NMR spectra, information confirms that the bonds between C₆ position of glucose units in cellulose and α-carbons of lignin side chain are benzyl ether linkage.

Key words: cellulose, ¹³C isotopic tracer, ¹³C NMR, lignin-carbohydrate complexes, benzyl ether linkage

CLC Number:

TQ35

XIANG Song-ming, XIE Yi-min, YANG Hai-tao, YAO Lan. Analysis of the Association between Cellulose and Lignin by Carbon 13 Tracer Method with Cellulose Precursor[J]. Chemistry and Industry of Forest Products, 2014, 34(1): 37-42.

References

[1] XIE Y M, YASUDA S, WU H, et al.Analysis of the structure of lignin-carbohydrate complexes by the specific ¹³C tracer method[J].Journal of Wood Science, 2000, 46(2):130-136.
[2] MCCABE B J, PREVIS S F.Using isotope tracers to study metabolism:Application in mouse models[J].Metabolic Engineering, 2004, 6(1):25-35.
[3] ALLEN D K, YAIR SHACHAR-HILL Y, OHLROGGE J B.Compartment-specific labeling information in ¹³C metabolic flux analysis of plants[J].Phytochemistry, 2007, 68(16/17/18):2197-2210.
[4] YANG H T, XIE Y M, YAO L, et al.On the Lignin-carbohydrate association in rice stalk by ¹³C isotopic tracer technique.Cellulose chemistry and technology[J].Cellulose Chemistry and Technology 2007, 41(7/8):363-369.
[5] 顾瑞军, 谢益民, 曾绍琼, 等.稻秆木素侧链 ¹³C 同位素示踪及固体¹³C NMR 分析[J].高等学校化学学报, 2002, 23(6):1073-1076
[6] XIE Y, TERASHIMA N.Selective carbon 13-enrichment of side chain carbons of ginkgo lignin traced by carbon 13 nuclear magnetic resonance[J].Mokuzai Gakkaishi, 1991, 37(10):935-941.
[7] XIE Y, GU R, WATANABE T.Studies on the linkages between dehydrogenation polymer and cell wall polysaccharide by carbon-13 isotopic tracer method[C]//Proceeding of 12th International Symposium on Wood and Pulping Chemistry, Madison:[s.n.], 2003:207-210.
[8] 王鹏, 谢益民, 范建云.果胶-木质素复合体化学结构¹³C 同位素示踪法的研究[J].陕西科技大学学报, 2006, 24(5):17-24.
[9] XIE Y, DANIELLE R, TERASHIMA N.Selective carbon 13 enrichment of side chain carbons of ginkgo lignin traced by carbon 13 nuclear magnetic resonance[J].Plant Physiology and Biochemistry, 1994, 32(2):234-249.
[10] STEPHEN Y L, CARLTON W D(Eds.).Methods in Lignin Chemistry[M].Berlin Heidelberg:Springer-Verlag press, 1992:68-74.
[11] SENIOR D J, HAMILTON J.Biobleaching with xylanases brings biotechnology to reality[J].Pulp & Paper, 1992, 66(9):111-114.
[12] DE J E, WONG K Y, SADDLER J N.The mechanism of xylanase prebleaching of kraft pulp:An examination using model pulps prepared by depositing lignin and xylan on cellulose fibers[J].Holzforschung, 1997, 51(1):19-26.
[13] DURANOVA M, HIRSCH J, KOLENOVA K, et al.Fungal glucuronoyl esterases and substrate uronic acid recognition[J].Bioscience, Biotechnology, and Biochemistry, 2009, 73(11):2483-2487.
[14] DINEV Z, AHMAD Z W, ROBERT T C, et al.A convenient gram-scale synthesis of uridine diphospho(¹³C6) glucose[J].Carbohydrate Research, 2006, 341(10):1743-1747.
[15] IMAI T, TERASHIMA N.Determination of the distribution and reaction of polysaccharide in wood cell wall by the isotopic tracer technique I.Selective radio-labeling of cell wall polysaccharide in Magnolia kobus[J].Mokuzai Gakkaishi, 1990, 36(11):917-922.
[16] BJÖRKMAN A.Lignin and lignin-carbohydrate complexes:Extraction from wood meal with neutral solvents[J].Industrial & Engineering Chemistry, 1957, 49(9):1395-1398.
[17] AZUMA J, KOSHIJIMA T.¹³C NMR spectroscopy of cellulose and related carbohydrates[J].Wood Research, 1981, 16:63-69.

Analysis of the Association between Cellulose and Lignin by Carbon 13 Tracer Method with Cellulose Precursor

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