Synthesis of Oligo-L-Tyrosine via Bromelain

doi:10.11944/j.issn.1000-0518.2020.02.190224

Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (2): 175-181.DOI: 10.11944/j.issn.1000-0518.2020.02.190224

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Synthesis of Oligo-L-Tyrosine via Bromelain

JIANG Xiaoxiao,ZHU Jinwen,LIAO Xiaofeng,YIN Weiwei,GAO Peng,YANG Changlin,WANG Feng()

Key Laboratory of Synthetic and Biological Colloids,Ministry of Education,School of Chemical and Material Engineering,Jiangnan University,Wuxi,Jiangsu 214122,China

Received:2019-08-21 Accepted:2019-11-04 Published:2020-02-01 Online:2020-02-06
Contact: WANG Feng
Supported by:
Supported by the National Scholarship for Studying Abroad(No.201406795023), the Postgraduate Research and Practice Innovation Program of Jiangsu Province(No.SJCX18-0618), and the National Undergraduate Innovation and Entrepreneurship Training Program(No.201910295049)

Abstract

Abstract:

Herein, oligo-L-tyrosine (O-L-Try) was synthesized from L-tyrosine methyl ester with bromelain as the catalyst. The maximal value of O-L-Try yield reached 65% under the optimum reaction conditions of 0.8 U/mL of bromelain, volume fraction 7.5% of dimethyl sulfoxide(DMSO) in phosphate solution (pH=7.5, 0.2 mol/L) and 0.23 g/mL of L-tyrosine methyl ester at 50 ℃ for five hours.The structure of O-L-Try was characterized by matrix-assisted laser desorption/ ionization time of flight mass spectrometry (MALDI-TOF-MS), hydrogen nuclear magnetic resonance spectroscopy (¹H NMR), Raman spectroscopy and Fourier transform infrared spectrometry (FTIR). The polymerization degree of O-L-Try is mainly 10 as measured by MALDI-TOF-MS. The average degree of polymerization of O-L-Try is 8 as determined by ¹H NMR analysis. Raman spectroscopy shows that O-L-Try has the characteristic peaks at 1623 cm^-1 (amide I band), 1447 cm^-1 (amide II band), 1270 cm^-1 (amide III band) and 648 cm^-1 (amide IV band).

Key words: bromelain catalysis, oligo-L-tyrosine, structure characterization

JIANG Xiaoxiao, ZHU Jinwen, LIAO Xiaofeng, YIN Weiwei, GAO Peng, YANG Changlin, WANG Feng. Synthesis of Oligo-L-Tyrosine via Bromelain[J]. Chinese Journal of Applied Chemistry, 2020, 37(2): 175-181.

References

[1]	Fetsch C,Grossmann A,Holz L,et al. Polypeptoids from N-Substituted Glycine N-Carboxyanhydrides:Hydrophilic, Hydrophobic, and Amphiphilic Polymers with Poisson Distribution[J]. Macromolecules,2011,44(17):6746-6758.
[2]	XU Xu,WU Guoli,ZHANG Jie,et al. Synthesis and Amphiphilic Property of Ethyleneglycol Functionalized Polyglutamate[J]. Acta Chim Sin,2008,66(9):1102-1106(in Chinese). 徐旭,伍国琳,张洁,等. 具有乙二醇侧链的聚谷氨酸酯的合成,表征及其两亲性[J]. 化学学报,2008,66(9):1102-1106.
[3]	Mallakpour S,Ayatollahi H,Sabzalian M R.Study on Biodegradability of Poly(amide-imide)s Containing N-Trimellitylimido-L-amino Acids and 3,5-Diamino-N-(pyridin-3-yl) Benzamide Linkages[J]. Polym Sci Ser B,2014,56(4):464-470.
[4]	Deming T J.Synthetic Polypeptides for Biomedical Applications[J]. Prog Polym Sci,2007,32(8/9):858-875.
[5]	Cai C,Lin J,Zhuang Z,et al. Ordering of Polypeptides in Liquid Crystals, Gels and Micelles[M]. Controlled Polymerization and Polymeric Structures:Springer,2013:159-199.
[6]	Yoshimitsu H,Kanazawa A,Kanaoka S,et al. Well-Defined Polymeric Ionic Liquids with an Upper Critical Solution Temperature in Water[J]. Macromolecules,2012,45(23):9427-9434.
[7]	Wang F,Zhu J,Yan T,et al. Amphiphilic Bromelain-Synthesized Oligo-Phenylalanine Grafted with Methoxypolyethylene Glycol Possessing Stabilizing Thermo-Responsive Emulsion Properties[J]. J Colloid Interface Sci,2019,538:1-14.
[8]	ZHAO Li,DING Jianxun,XIAO Chunsheng,et al. Poly(L-glutamic acid) Microsphere:Preparation and Application in Oral Drug Controlled Release[J]. Acta Chim Sin,2015,73:60-65(in Chinese). 赵丽,丁建勋,肖春生,等. 聚(L-谷氨酸) 微球的制备及其口服药物控释研究[J]. 化学学报,2015,73:60-65.
[9]	LIU Yanhua,HUANG Dengfa,ZHU Jinwen,et al. Enzymatic Synthesis of L-Phenylalanine Polypeptide[J]. Chemistry,2018,81(4):361-365(in Chinese). 刘严华,黄登发,朱锦雯,等. L-苯丙氨酸聚肽的酶催化合成[J]. 化学通报,2018,81(4):361-365.
[10]	Vlakh E,Ananyan A,Zashikhina N,et al. Preparation, Characterization, and Biological Evaluation of Poly(Glutamic acid)-b-Polyphenylalanine Polymersomes[J]. Polymers,2016,8(6):212.
[11]	Wang Z,Yan Y,Wang Y,et al. The Interaction Between CSE/H2S and the iNOS/NO-mediated Resveratrol/Poly(ethylene glycol)-Poly(phenylalanine) Complex Alleviates Intestinal Ischemia/Reperfusion Injuries in Diabetic Rats[J]. Biomed Pharmacother,2019,112:108736.
[12]	LIN Lin,GUO Zhaopei,CHEN Jie,et al. Synthesis and Characterization of Polyphenylalanine Grafted Low Molecular Weight PEI as Efficient Gene Carriers[J]. Acta Polym Sin,2017,2(2):321-328(in Chinese). 林琳,郭兆培,陈杰,等. 聚苯丙氨酸修饰低相对分子质量聚乙烯亚胺制备高效基因载体[J]. 高分子学报,2017,2(2):321-328.
[13]	Patel M,Nakaji-Hirabayashi T,Matsumura K.Effect of Dual-drug-releasing Micelle-Hydrogel Composite on Wound Healing in Vivo in Full-Thickness Excision Wound Rat Model[J]. J Biomed Mater Res Part A,2019,107(5):1094-1106.
[14]	Gu X,Wei Y,Fan Q,et al. cRGD-decorated Biodegradable Polytyrosine Nanoparticles for Robust Encapsulation and Targeted Delivery of Doxorubicin to Colorectal Cancer in Vivo[J]. J Controlled Release,2019,301:110-118.
[15]	Gu X,Qiu M,Sun H,et al. Polytyrosine Nanoparticles Enable Ultra-High Loading of Doxorubicin and Rapid Enzyme-Responsive Drug Release[J]. Biomater Sci,2018,6(6):1526-1534.
[16]	Gao Y,Cranston R.Polytyrosine as an Electroactive Lebel for Signal Amplification in Electrochemical Immunosensors[J]. Anal Chim Acta,2010,659(1):109-114.
[17]	Eguílaz M,Gutierrez F,González-Domínguez J M,et al. Single-Walled Carbon Nanotubes Covalently Functionalized with Polytyrosine:A New Material for the Development of NADH-Based Biosensors[J]. Biosens Bioelectron,2016,86:308-314.
[18]	Stewart J M.Bradykinin in Solid-Phase Peptide Synthesis[J]. Int J Pept Res Ther,2007,13(1/2):3-5.
[19]	YU Shufang,GU Xin,WU Guolin,et al. Preparation and pH-Sensitive Drug Delivery Study of mPEGpoly(Imidazole Propyl-Asparagine)-Poly(L-Alanine)[J]. Acta Chim Sin,2012,70(2):177-182(in Chinese). 于树芳,顾鑫,伍国琳,等. 乙二醇-聚 (咪唑丙基-天冬酰胺)-聚丙氨酸三嵌段共聚物的合成及其pH-响应性药物控制释放性能的研究[J]. 化学学报,2012,70(2):177-182.
[20]	Lombard C,Saulnier J,Wallach J.Recent Trends in Protease-Catalyzed Peptide Synthesis[J]. Protein Pept Lett,2005,12(7):621-629.
[21]	Yu B,Zhang A,Zhang M,et al. Current Status and Future Developments in Synthetic Peptides[J]. Curr Org Chem,2018,22(20):1951-1958.
[22]	Tsuchiya K,Miyagi Y,Miyamoto T,et al. Synthesis of Polypeptides:Enzymatic Polymerization Towards Green Polymer Chemistry[M]. Singapore:Springer,2019:233-265.
[23]	Ulijn R V,Baraga a B,Halling P J,et al. Protease-Catalyzed Peptide Synthesis on Solid Support[J]. J Am Chem Soc,2002,124(37):10988-10989.
[24]	Viswanathan K,Omorebokhae R,Li G,et al. Protease-Catalyzed Oligomerization of Hydrophobic Amino Acid Ethyl Esters in Homogeneous Reaction Media Using L-Phenylalanine as a Model System[J]. Biomacromolecules,2010,11(8):2152-2160.
[25]	Dabkowska A P,Foglia F,Lawrence M J,et al. On the Solvation Structure of Dimethylsulfoxide/Water Around the Phosphatidylcholine Head Group in Solution[J]. J Chem Phys,2011,135(22):225105.
[26]	Zhang L Q,Xu L,Yang X C,et al. Lipase-Catalyzed Synthesis of Precursor Dipeptides of RGD in Aqueous Water-Miscible Organic Solvents[J]. Prep Biochem Biotechnol,2003,33(1):1-12.
[27]	Fukuoka T,Tachibana Y,Tonami H,et al. Enzymatic Polymerization of Tyrosine Derivatives. Peroxidase- and Protease-Catalyzed Synthesis of Poly(tyrosine)s with Different Structures[J]. Biomacromolecules,2002,3(4):768-774.

Synthesis of Oligo-L-Tyrosine via Bromelain

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