全细胞催化法生产N-乙酰神经氨酸的研究进展

doi:10.13560/j.cnki.biotech.bull.1985.2015.03.020

摘要/Abstract

摘要： N-乙酰神经氨酸（N-acetyl-D-neuraminic acid，Neu5Ac）及其衍生物不仅在人体内发挥重要的生理生化功能，且已经应用到流感的预防和治疗。但已有的N-乙酰神经氨酸生产方法产量低、成本高，限制了其大规模生产和广泛应用。随着分子生物学技术及糖组学研究的发展与成熟，一种新型的生物技术即全细胞催化法生产N-乙酰神经氨酸正成为研究的热点。旨在介绍全细胞催化技术合成N-乙酰神经氨酸的研究进展。

Abstract: N-acetyl-D-neuraminic acid and its derivatives have versatile biological functions and considerable contribution in the therapeutics field. But the production and wide applications of Neu5Ac are limited by the low yield and high cost. With the development of Molecular Biology and the research of Glycomics, the production Neu5Ac by whole-cell biocatalysis, a novel type of biocatalysis, has attracted researchers’ attention. In this paper, we report that the advances in production of Neu5Ac by whole-cell biocatalysis, and also propose some guidelines for future studies.

张丛丛,陈彩霞,陈笑,温雅,晏礼明,陶勇. 全细胞催化法生产N-乙酰神经氨酸的研究进展[J]. 生物技术通报, 2015, 31(4): 175-183.

Zhang Congcong, Chen Caixia, Chen Xiao, Wen Ya, Yan Liming, Tao Yong. Advances in Production of N-acetyl-D-neuraminic Acid by #br#Whole-cell Biocatalysis [J]. Biotechnology Bulletin, 2015, 31(4): 175-183.

参考文献

[1] Chen X, Varki A. Advances in the biology and chemistry of sialic acids［J］. ACS Chemical Biology, 2009, 5（2）：163-176.
[2] Schauer R. Biochemistry and role of sialic acids［M］// Rosenberg A. Biology of the Sialic Acids. New York：Plenum Publishing Corporation, 1995：57-67.
[3] Tao F, Zhang Y, Ma C, et al. Biotechnological production and applications of N-acetyl-D-neuraminic acid：current state and perspectives［J］. Applied Microbiology and Biotechnology, 2010, 87（4）：1281-1289.
[4] Yu R, Ledeen R. Configuration of the ketosidic bond of sialic acid［J］. Journal of Biological Chemistry, 1969, 244（5）：1306-1313.
[5] Rosenberg A, Schengrund CL. Biological roles of sialic acid［M］. New York：Plenum Publishing Corporation, 1976.
[6] Varki A. Diversity in the sialic acids［J］. Glycobiology, 1992, 2（1）：25-40.
[7] Reuter G, Gabius HJ. Sialic acids structure analysis metabolism occurrence recognition［J］. Biological Chemistry Hoppe-Seyler, 1996, 377（6）：325-342.
[8] Schauer R. Sialic acids as regulators of molecular and cellular inter-actions［J］. Current Opinion in Structural Biology, 2009, 19（5）：507-514.
[9] Schauer R. Achievements and challenges of sialic acid research
［J］. Glycoconjugate Journal, 2000, 17（7-9）：485-499.
[10] Hu S, Chen J, Yang Z, et al. Coupled bioconversion for preparation of N-acetyl-D-neuraminic acid using immobilized N-acetyl-D-glucosamine-2-epimerase and N-acetyl-D-neuraminic acid lyase［J］. Applied Microbiology and Biotechnology, 2010, 85（5）：1383-1391.
[11] Kelm S, Schauer R, Crocker P. The Sialoadhesins—a family of sialic acid-dependent cellular recognition molecules within the immunoglobulin superfamily［J］. Glycoconjugate Journal, 1996, 13（6）：913-926.
[12] Kelm S, Schauer R. Sialic acids in molecular and cellular interactions［J］. International Review of Cytology, 1997, 175：137-240.
[13] B?hm S, Schwab I, Lux A, et al. The role of sialic acid as a modulator of the anti-inflammatory activity of IgG［J］. Seminars in Immunopathology, 2012, 34（3）：443-453.
[14] Oriquat GA, Saleem TH, Abdullah, ST, et al. Soluble CD14, sialic acid and L-fucose in breast milk and their role in increasing the immunity of breast-fed infants［J］. American Journal of Biochemistry and Biotechnology, 2011, 7（1）：21-28.
[15] Wielga P, Braszko JJ. The participation of sialic acids in microglia–neuron interactions［J］. Cellular Immunology, 2012, 273（1）：17-22.
[16] Sprenger N, Julita M, Donnicola D, et al. Sialic acid feeding aged rats rejuvenates stimulated salivation and colon enteric neuron chemotypes［J］. Glycobiology, 2009, 19（12）：1492-1502.
[17] Varki NM, Varki A. Diversity in cell surface sialic acid presentations：implications for biology and disease［J］. Laboratory Investigation, 2007, 87（9）：851-857.
[18] Bondioli L, Ruozi B, Belletti D, et al. Sialic acid as a potential approach for the protection and targeting of nanocarriers［J］. Expert Oopinion on Drug Delivery, 2011, 8（7）：921-937.
[19] Blix F, Gottschalk A, Klenk E. Proposed nomenclature in the field of neuraminic and sialic acids［J］. Nature, 1957, 179：1088.
[20] Juneja LR, Koketsu M, Nishimoto K, et al. Large-scale preparation of sialic-acid from chalaza and egg-yolk membrane［J］. Carbohydrate Research, 1991, 214（1）：179-186.
[21] Schaue R, Stoll S, Reuter G. Differences in the amount of N-acetyl-and N-glycoloyl-neuraminic acid, as well as O-acylated sialic acids, of fetal and adult bovine tissues［J］. Carbohydrate Research, 1991, 213：353-359.
[22] Koketsu M, Juneja LR, Kawanami H, et al. Preparation of N-acetylneuraminic acid from delipidated egg yolk［J］. Glycoconjugate Journal, 1992, 9（2）：70-74.
[23] Furuhata K. Chemistry of N-acetylneuraminic acid（Neu5Ac）［J］. Trends Glycosci Glycotechnol, 2004, 16：143-169.
[24] Cornforth J, Firth M, Gottschalk A. The synthesis of N-acetylneura-minic acid［J］. Biochemical J, 1958, 68（1）：57.
[25] Chan TH, Lee MC. Indium-mediated coupling of α-（Bromomethyl） acrylic acid with carbonyl compounds in aqueous media. concise syntheses of（+）-3-Deoxy-D-glycero-D-galacto- nonulosonic acid and N-acetylneuraminic acid［J］. The Journal of Organic Chemistry, 1995, 60（13）：4228-4232.
[26] Danishefsky SJ, DeNinno MP, Chen SH. Stereoselective total synth-eses of the naturally occurring enantiomers of N-acetylneuraminic acid and 3-deoxy-D-manno-2-octulosonic acid. A new and stereos-pecific approach to sialo and 3-deoxy-D-manno-2-octulosonic acid conjugates［J］. Journal of the American Chemical Society, 1988, 110（12）：3929-3940.
[27] Haag-Zeino B, Schmidt RR. De novo synthesis of carbohydrates and related natural products, 34. Synthesis of N-acetyl-β-D-neuraminic acid derivatives via inverse-type hetero-Diels-Alder reaction［J］. Liebigs Annalen der Chemie, 1990, 1990（12）：1197-1203.
[28] 郭明, 胡昌华. 生物转化—从全细胞催化到代谢工程［J］. 中国生物工程杂志, 2010, 30：110-115.
[29] Plumbridge J, Vimr E. Convergent pathways for utilization of the amino sugars N-acetylglucosamine, N-acetylmannosamine, and N-acetylneuraminic acid by Escherichia coli［J］. Journal of bacteriology, 1999, 181（1）：47-54.
[30 Vimr ER, Kalivoda KA, Deszo EL, et al. Diversity of microbial sialic acid metabolism［J］. Microbiology and Molecular Biology Reviews, 2004, 68（1）：132-153.
[31] Ferrero Má, Aparicio LR. Biosynthesis and production of polysialic acids in bacteria［J］. Applied Microbiology and Biotechnology, 2010, 86（6）：1621-1635.
[32] Sun W, Ji W, Li N, et al. Construction and expression of a polycistronic plasmid encoding N-acetylglucosamine 2-epimerase and N-acetylneuraminic acid lyase simultaneously for production of N-acetylneuraminic acid［J］. Bioresource Technology, 2013, 130：23-29.
[33］Li Y, Yu H, Cao H, et al. Pasteurella multocida sialic acid aldolase：
a promising biocatalyst［J］. Applied Microbiology and Biotechnology, 2008, 79（6）：963-970.
[34] North RA, Kessans SA, Atkinson SC, et al. Cloning, expression, purification, crystallization and preliminary X-ray diffraction studies of N-acetylneuraminate lyase from methicillin-resistant Staphylococcus aureus［J］. Acta Crystallogr Sect F, 2013, 69（3）：306-312.
[35] Maru I, Ohta Y, Murata K, et al. Molecular cloning and identification of N-acyl-D-glucosamine 2-epimerase from porcine kidney as a renin-binding protein［J］. Journal of Biological Chemistry, 1996, 271（27）：16294-16299.
[36] Sola-Carvajal A, Sánchez-Carrón G, García-García MI, et al. Properties of BoAGE2, a second N-acetyl-D-glucosamine 2-epimerase from Bacteroides ovatus ATCC 8483［J］. Biochimie, 2012, 94（1）：222-230.
[37] Tabata K, Koizumi S, Endo T, et al. Production of N-acetyl-D-neuraminic acid by coupling bacteria expressing N-acetyl- D-glucosamine 2-epimerase and N-acetyl-D-neuraminic acid synthetase［J］. Enzyme and Microbial Technology, 2002, 30（3）：327-333.
[38] Xu P, Qiu JH, Zhang YN, et al. Efficient whole-cell biocatalytic synthesis of N-acetyl-D- neuraminic acid［J］. Advanced Synthesis & Catalysis, 2007, 349（10）：1614-1618.
[39] Hao J, Ma C, Gao C, et al. Pseudomonas stutzeri as a novel biocatalyst for pyruvate production from DL-lactate［J］. Biotechnology Letters, 2007, 29（1）：105-110.
[40] Lee YC, Wu HM, Wang WC, et al. The central cavity from the（α/α）6 barrel structure of Anabaena sp. CH1 N-acetyl-D- glucosamine 2-epimerase contains two key histidine residues for reversible conversion［J］. Journal of Molecular Biology, 2007, 367（3）：895-908.
[41] Lee YC, Chien HC, Hsu WH. Production of N-acetyl-D-neuraminic acid by recombinant whole cells expressing Anabaena sp. CH1 N-acetyl-D-glucosamine 2-epimerase and Escherichia coli N-acetyl-D-neuraminic acid lyase［J］. Journal of Biotechnology, 2007, 129（3）：453-460.
[42] Zhang YN, Tao F, Du MF, et al. An efficient method for N-acetyl-D-neuraminic acid production using coupled bacterial cells with a safe temperature-induced system［J］. Applied Microbiology and Biotechnology, 2010, 86（2）：481-489.
[43] Ishikawa M, Koizumi S. Microbial production of N-acetylneuraminic acid by genetically engineered Escherichia coli［J］. Carbohydrate Research, 2010, 345（18）：2605-2609.
[44] Tao F, Zhang YN, Ma CQ, et al. One-pot bio-synthesis：N-acetyl-D-neuraminic acid production by a powerful engineered whole-cell catalyst［J］. Scientific Reports, 2011, 1：142.
[45] Kang J, Gu P, Wang Y, et al. Engineering of an N-acetylneuraminic acid synthetic pathway in Escherichia coli［J］. Metabolic Engin-eering, 2012, 14（6）：623-629.
[46] Lin BX, Zhang ZJ, Liu WF, et al. Enhanced production of N-acetyl-D-neuraminic acid by multi-approach whole-cell biocatalyst［J］. Applied Microbiology and Biotechnology, 2013, 97（11）：4775-4784.