Research progress in the effect of additives on the polymorphic crystallization of amino acids in solution

doi:10.16085/j.issn.1000-6613.2020-1787

Abstract

Abstract:

Different polymorphs of the amino acid often show different physicochemical properties and medicinal effectiveness. Therefore, it is very important to obtain the target polymorphs by regulating the polymorphic crystallization process of amino acid in solution, in which the influence of additives is direct and effective. Thus, in this paper, the effects of various kinds of additives on the process of polymorphic crystallization of amino acid in solution were reviewed. First of all, taking the γ-glycine as an example which couldn’t be directly obtained from aqueous solution, the promoting effects of acid, alkali and inorganic salt on the nucleation of the crystal were elucidated, and the mechanism for the effectiveness of these additives on the growth of different polymorphs was analyzed on the perspective of charge compensation. Secondly, the influences of tailor-made additives on the crystal morphology and polymorph of amino acids were expounded. Specifically, the influence of tailor-made additives with different structures on polymorphic transformation was analyzed. Then, the selectivity effects of ethanol-water solvent on the polymorphic crystallization of different amino acids were introduced. Finally, based on the above analysis, the preparation of different target crystal forms by molecular design of additives was prospected.

Key words: amino acid, solution crystallization, polymorphs, additives

摘要：

氨基酸的不同晶型往往表现出不同的理化性质和药用效果。因此通过调控氨基酸多晶型溶液结晶过程得到目标晶型非常重要，其中添加剂对不同晶型的影响直接且有效，是控制晶型生产常采用的手段。本文综述了不同种类添加剂对氨基酸多晶型溶液结晶过程的影响。首先，以水溶液中不能直接得到的甘氨酸γ晶型为例，阐明了酸、碱和无机盐对其成核的促进作用，从电荷补偿角度分析了该类添加剂对不同晶型生长过程的影响机理。其次，阐述了tailor-made添加剂对氨基酸晶体形态和晶型的调控作用，重点分析了不同结构的tailor-made添加剂对晶型转变的影响规律。介绍了醇-水等混合溶剂对不同氨基酸多晶型结晶过程的选择性影响。最后，在以上分析的基础上，对通过添加剂分子设计制备不同目标晶型进行了展望。

关键词: 氨基酸, 溶液结晶, 多晶型, 添加剂

CLC Number:

O742⁺.4

SU Weiyi, LIU Xing, HAO Qi, GUO Pan, HAO Hongxun, LI Chunli. Research progress in the effect of additives on the polymorphic crystallization of amino acids in solution[J]. Chemical Industry and Engineering Progress, 2021, 40(8): 4463-4472.

苏伟怡, 刘星, 郝琪, 郭攀, 郝红勋, 李春利. 添加剂对氨基酸多晶型溶液结晶过程影响的研究进展[J]. 化工进展, 2021, 40(8): 4463-4472.

Figures/Tables 5

References 62

1	CHEN J, SARMA B, EVANS J M B, et al. Pharmaceutical crystallization[J]. Crystal Growth & Design, 2011, 11(4): 887-895.
2	BROG J P, CHANEZ C L, CROCHET A, et al. Polymorphism, what it is and how to identify it: a systematic review[J]. RSC Advances, 2013, 3(38): 16905-16931.
3	陈桂良, 李君婵, 彭兴盛, 等. 药物晶型及其质量控制[J]. 药物分析杂志, 2012, 32(8): 1503-1508, 1485.
	CHEN Guiliang, LI Junchan, PENG Xingsheng, et al. Drug polymorphism and related quality control[J].Chinese Journal of Pharmaceutical Analysis, 2012, 32(8): 1503-1508, 1485.
4	杨世颖, 周健, 张丽, 等. 我国化学药物晶型研究现状与进展[J]. 医药导报, 2019, 38(2): 177-182.
	YANG Shiying, ZHOU Jian, ZHANG Li, et al. Present situation and progress of the research for polymorphic chemical drugs in China[J]. Herald of Medicine, 2019, 38(2): 177-182.
5	WENG J Y, HUANG Y P, HAO D L, et al. Recent advances of pharmaceutical crystallization theories[J]. Chinese Journal of Chemical Engineering, 2020, 28(4): 935-948.
6	HATAKKA H, ALATALO H, LOUHI-KULTANEN M, et al. Closed-loop control of reactive crystallization part II: polymorphism control of L-glutamic acid by sonocrystallization and seeding[J]. Chemical Engineering & Technology, 2010, 33(5): 751-756.
7	WU C S, HSIEH P Y, YUYAMA K I, et al. Pseudopolymorph control of L-phenylalanine achieved by laser trapping[J]. Crystal Growth & Design, 2018, 18(9): 5417-5425.
8	WEISSBUCH I, TORBEEV V Y, LEISEROWITZ L, et al. Solvent effect on crystal polymorphism: why addition of methanol or ethanol to aqueous solutions induces the precipitation of the least stable β form of glycine[J]. Angewandte Chemie International Edition, 2005, 44(21): 3226-3229.
9	DING L, ZONG S H, DANG L P, et al. Effects of inorganic additives on polymorphs of glycine in microdroplets[J]. CrystEngComm, 2018, 20(2): 164-172.
10	SONG R Q, CÖLFEN H. Additive controlled crystallization[J]. CrystEngComm, 2011, 13(5): 1249-1276.
11	尚泽仁, 胡卫国, 汤伟伟, 等. 离子液体在药物晶体工程中的应用[J]. 化工进展, 2019, 38(5): 2389-2401.
	SHANG Zeren, HU Weiguo, TANG Weiwei, et al. Application of ionic liquids in pharmaceutical crystal engineering[J]. Chemical Industry and Engineering Progress, 2019, 38(5): 2389-2401.
12	KITAMURA M. Controlling factor of polymorphism in crystallization process[J]. Journal of Crystal Growth, 2002, 237/238/239: 2205-2214.
13	KITAMURA M. Strategy for control of crystallization of polymorphs[J]. CrystEngComm, 2009, 11(6): 949-964.
14	WU G Y. Amino acids: metabolism, functions, and nutrition[J]. Amino Acids, 2009, 37(1): 1-17.
15	张金龙, 王静康, 尹秋响. 氨基酸的提取与精制[J]. 化学工业与工程, 2004, 21(2): 101-106.
	ZHANG Jinlong, WANG Jingkang, YIN Qiuxiang. Extraction and separation of amino acid[J]. Chemical Industry and Engineering, 2004, 21(2): 101-106.
16	HE G W, BHAMIDI V, WILSON S R, et al. Direct growth of γ-glycine from neutral aqueous solutions by slow, evaporation-driven crystallization[J]. Crystal Growth & Design, 2006, 6(8): 1746-1749.
17	KITAMURA M. Crystallization behavior and transformation kinetics of L-histidine polymorphs[J]. Journal of Chemical Engineering of Japan, 1993, 26(3): 303-307.
18	FERRARI E S, DAVEY R J. Solution-mediated transformation of α to β L-glutamic acid: rate enhancement due to secondary nucleation[J]. Crystal Growth & Design, 2004, 4(5): 1061-1068.
19	CASHELL C, CORCORAN D, HODNETT B K. Secondary nucleation of the β-polymorph of L-glutamic acid on the surface of α-form crystals[J]. Chemical Communications, 2003(3): 374-375.
20	HAN G J, THIRUNAHARI S, CHOW P S, et al. Resolving the longstanding riddle of pH-dependent outcome of glycine polymorphic nucleation[J]. CrystEngComm, 2013, 15(6): 1218-1224.
21	TOWLER C S, DAVEY R J, LANCASTER R W, et al. Impact of molecular speciation on crystal nucleation in polymorphic systems: the conundrum of γ-glycine and molecular ‘self poisoning’[J]. Journal of the American Chemical Society, 2004, 126(41): 13347-13353.
22	HAN G J, CHOW P S, TAN R B H. Direct comparison of α- and γ-glycine growth rates in acidic and basic solutions: new insights into glycine polymorphism[J]. Crystal Growth & Design, 2012, 12(5): 2213-2220.
23	HAMMOND R B, RAMACHANDRAN V, ROBERTS K J. Molecular modelling of the incorporation of habit modifying additives: α-glycine in the presence of L-alanine[J]. CrystEngComm, 2011, 13(15): 4935-4944.
24	TORBEEV V Y, SHAVIT E, WEISSBUCH I, et al. Control of crystal polymorphism by tuning the structure of auxiliary molecules as nucleation inhibitors. the β-polymorph of glycine grown in aqueous solutions[J]. Crystal Growth & Design, 2005, 5(6): 2190-2196.
25	YANG X, LU J, WANG X J, et al. Effect of sodium chloride on the nucleation and polymorphic transformation of glycine[J]. Journal of Crystal Growth, 2008, 310(3): 604-611.
26	HRKOVAC M, KARDUM J P, SCHUSTER A, et al. Influence of additives on glycine crystal characteristics[J]. Chemical Engineering & Technology, 2011, 34(4): 611-618.
27	HRKOVAC M, PRLIC KARDUM J, UKRAINCZYK N. Influence of NaCl on granulometric characteristics and polymorphism in batch-cooling crystallization of glycine[J]. Chemical Engineering & Technology, 2015, 38(1): 139-146.
28	AZHAGAN S A C, KATHIRAVAN V S, PRIYA N S. Crystallization, habit modification and control of nucleation of glycine polymorphs from aqueous solutions doped with magnesium sulfate impurity[J]. Materials Science-Poland, 2018, 36(3): 483-493.
29	SEKAR C, PARIMALADEVI R. Effect of KCl addition on crystal growth and spectral properties of glycine single crystals[J]. Spectrochimica Acta Part A, 2009, 74(5): 1160-1164.
30	HAN G J, CHOW P S, TAN R B H. Effects of common inorganic salts on glycine polymorphic transformation: an insight into salt-dependent polymorphic selectivity[J]. Crystal Growth & Design, 2016, 16(11): 6499-6505.
31	HAN G J, CHOW P S, TAN R B H. Salt-dependent growth kinetics in glycine polymorphic crystallization[J]. CrystEngComm, 2016, 18(3): 462-470.
32	DUFF N, DAHAL Y R, SCHMIT J D, et al. Salting out the polar polymorph: analysis by alchemical solvent transformation[J]. The Journal of Chemical Physics, 2014, 140(1): 014501.
33	RENUKA DEVI K, SRINIVASAN K. The role of charge compensation on the nucleation of α and γ polymorphs of glycine from aqueous solution[J]. Journal of Crystal Growth, 2013, 364: 88-94.
34	RENUKA DEVI K, SRINIVASAN K. Towards a better understanding of the nucleation behavior of α and γ polymorphs of glycine from aqueous solution in the presence of selective additives by charge compensation mechanism[J]. Journal of Crystal Growth, 2014, 401: 227-232.
35	LOSEV E A, MIKHAILENKO M A, ACHKASOV A F, et al. The effect of carboxylic acids on glycine polymorphism, salt and co-crystal formation. A comparison of different crystallisation techniques[J]. New Journal of Chemistry, 2013, 37(7): 1973-1981
36	RENUKA DEVI K, SRINIVASAN K. Impact of malonic acid on the segregation of glycine polymorphs-analytical assisted molecular approach[J]. Crystal Research and Technology, 2015, 50(2): 171-178.
37	LIU X Y. Interfacial structure analysis for the prediction of morphology of crystals and implications for the design of tailor-made additives[J]. Journal of Crystal Growth, 1997, 174(1/2/3/4): 380-385.
38	WEISSBUCH I, POPOVITE-BIRO R, LAHAV M, et al. Understanding and control of nucleation, growth, habit, dissolution and structure of two- and three-dimensional crystals using “tailor-made” auxiliaries[J]. Acta Crystallographica Section B: Structural Science, 1995, 51(2): 115-148.
39	DOWLING R, DAVEY R J. CURTIS R A.et al. Acceleration of crystal growth rates: an unexpected effect of tailor-made additives[J]. Chemical Communications, 2010, 46(32): 5924-5926.
40	LEE S H, LEE G H, LEE K H, et al. In situ tailor-made additives for molecular crystals: a simple route to morphological crystal engineering[J]. Crystal Growth & Design, 2016, 16(7): 3555-3561.
41	CONSTANCE E N, MOHAMMED M, MOJIBOLA A, et al. Effect of additives on the crystal morphology of amino acids: a theoretical and experimental study[J]. The Journal of Physical Chemistry C, 2016, 120(27): 14749-14757.
42	PALANISAMY D, KARUPPANNAN S. Nucleation control and growth of metastable α-L-glutamic acid single crystals in the presence of L-phenylalanine[J]. Procedia Engineering, 2016, 141: 70-77.
43	DHANASEKARAN P, SRINIVASAN K. Nucleation control, separation and bulk growth of metastable α-L-glutamic acid single crystals in the presence of L-tyrosine[J]. Journal of Crystal Growth, 2013, 364: 23-29.
44	LLINAS A, GOODMAN J M. Polymorph control: past, present and future[J]. Drug Discov Today, 2008, 13(5/6): 198-210.
45	LI Z H, SHI P, YANG Y, et al. Tuning crystallization and stability of the metastable polymorph of DL-methionine by a structurall similar additive[J]. CrystEngComm, 2019, 21(24): 3731-3739.
46	WANG L Y, TANG W W, DU S C, et al. Additive-induced slective crystallization of the elusive form-Ⅱ of γ-aminobutyric acid[J]. Chemical Engineering & Technolgy, 2020, 43(6): 1137-1143.
47	KITAMURA M, ISHIZU T. Kinetic effect of L-phenylalanine on growth process of L-glutamic acid polymorph[J]. Journal of Crystal Growth, 1998, 192(1/2): 225-35.
48	YANI Y, CHOW P S, TAN R B H. Molecular simulation study of the effect of various additives on salbutamol sulfate crystal habit[J]. Molecular Pharmaceutics, 2011, 8(5): 1910-1918.
49	YANG X Y, QIAN G, DUAN X Z, et al. Effect of impurity on the lateral crystal growth of L-alanine: a combined simulation and experimental study[J]. Industrial & Engineering Chemistry Research, 2012, 51(45): 14845-14849.
50	YANG X Y, QIAN G, DUAN X Z, et al. Impurity effect of L-valine on L-alanine crystal growth[J]. Crystal Growth & Design, 2013, 13(3): 1295-1300.
51	LIANG S S, DUAN X Z, ZHANG X Y, et al. Insights into polymorphic transformation of L-glutamic acid: a combined experimental and simulation study[J]. Crystal Growth & Design, 2015, 15(8): 3602-3608.
52	POLAT S, SAYAN P. Kinetic analysis and polymorphic phase transformation of glycine in the presence of lauric acid[J]. Journal of Crystal Growth, 2018, 481: 71-79.
53	POLAT S, SAYAN P. The characterization and polymorphism of α-glycine in the presence of butyric acid[J]. Advanced Powder Technology, 2018, 29(9): 1968-1976.
54	POLAT S, SAYAN P. Evaluation of solvent-mediated phase transformation of glycine using oleic acid: morphology and characterization study[J]. Chinese Journal of Chemical Engineering, 2018, 26(9): 1829-1836.
55	DAVEY R J, BLAGDEN N, POTTS G D, et al. Polymorphism in molecular crystals: stabilization of a metastable form by conformational mimicry[J]. Journal of the American Chemical Society, 1997, 119(7): 1767-1772.
56	CASHELL C, CORCORAN D, HODNETT B K. Effect of amino acid additives on the crystallization of L-glutamic acid[J]. Crystal Growth & Design, 2005, 5(2): 593-597.
57	MO Y X, DANG L P, WEI H Y. L-glutamic acid polymorph control using amino acid additives[J]. Industrial & Engineering Chemistry Research, 2011, 50(18): 10385-10392.
58	KELLEHER J M, LAWRENCE S E, MCAULIFFE M T, et al. Monomeric and polymeric derivatives of 5-aminoisophthalic acid as selective inhibitors of the β-polymorph of L-glutamic acid[J]. CrystEngComm, 2007, 9(1): 72-77.
59	RUSIN M, EWAN B C R, RISTIC R I. The glycine-stimulated nucleation and solution-mediated polymorphic transformation of L-glutamic acid[J]. CrystEngComm, 2013, 15(12): 2192-2196.
60	黄炎, 孙海龙, 孟子超, 等. 溶析结晶在医药领域的研究进展[J]. 化工进展, 2019, 38 (5): 2380-2388.
	HUANG Yan, SUN Hailong, MENG Zichao, et al. Progress in antisolvent crystallization in pharmaceutical field[J]. Chemical Industry and Engineering Progress, 2019, 38 (5): 2380-2388.
61	PUNMALEE N, WANTHA L, FLOOD A E. Antisolvent crystallization of polymorphs of L-histidine[J]. Chemical Engineering & Technology, 2018, 41(6): 1132-1138.
62	ROELANDS C P M, JIANG S F, KITAMURA M, et al. Antisolvent crystallization of the polymorphs of L-histidine as a function of supersaturation ratio and of solvent composition[J]. Crystal Growth & Design, 2006, 6(4): 955-963.

[1]	KANG Yu, GOU Zenian. Kinetics studies of carbon gas hydrate separation in the presence of amino acids and DTAC [J]. Chemical Industry and Engineering Progress, 2023, 42(10): 5067-5075.
[2]	QIN Jian, LIU Tianxia, WANG Jian, LU Xing. Preparation and tribological properties of oleic acid modified graphene/molybdenum disulfide composite lubricating additives [J]. Chemical Industry and Engineering Progress, 2022, 41(9): 4973-4985.
[3]	ZHANG Saihui, LI Xiaoyang, GAO Hui, WANG Lili. Recent progress in additives in interfacial polymerization for the preparation of polyamide composite membrane [J]. Chemical Industry and Engineering Progress, 2022, 41(9): 4884-4894.
[4]	LI Yeqing, YANG Xingru, LIANG Zhuo, JIANG Hao, XU Quan, ZHOU Hongjun, FENG Lu. Impact of exogenous additives on hydrothermal dechlorination performance of polyvinyl chloride [J]. Chemical Industry and Engineering Progress, 2022, 41(5): 2706-2712.
[5]	FANG Yufei, DING Donghai, XIAO Guoqing, FU Pengcheng, ZHONG Xiaochuan, ZHU Xianfeng. Progress in academic and application researches on ceramic proppant [J]. Chemical Industry and Engineering Progress, 2022, 41(5): 2511-2525.
[6]	QI Zhenhua, ZHOU Rong, BAI Yanan, LI Yuqin, TANG Yufang. Fermentation wastewater treatment and high-quality protein production by Chlorella pyrenoidosa under fed-batch mode [J]. Chemical Industry and Engineering Progress, 2022, 41(12): 6733-6743.
[7]	LYU Penggang, LIU Tao, YE Hang, HUANG Xiaoliang, DUAN Hongchang, TAN Zhengguo. Advances in improving the performance of additives for increasing propylene production in FCC process [J]. Chemical Industry and Engineering Progress, 2022, 41(1): 210-220.
[8]	PAN Yi, XU Minglei, HOU Bing, GUO Qi, YANG Shuangchun, KANTOMA Daniel Bala. Research progress of temperature-sensitive polymer in oil and gas production [J]. Chemical Industry and Engineering Progress, 2021, 40(4): 2109-2119.
[9]	JU Shuyun, WU Jianping, YANG Lirong. Advances in the molecular modification and application of D-amino acid oxidase [J]. Chemical Industry and Engineering Progress, 2021, 40(3): 1215-1225.
[10]	SUN Yue, LIU Lingling, LI Xinquan, PAN Jianfeng, LIU Jiabin. Research progress in mechanisms and effects of various additives used for preparing electrolytic copper foils [J]. Chemical Industry and Engineering Progress, 2021, 40(11): 5861-5874.
[11]	Zhenguo ZHANG, Xitao LIU, Ling LAI, Xiujuan FENG. Progress in degradation of chlorinated organic pollutants by mechanochemical method [J]. Chemical Industry and Engineering Progress, 2021, 40(1): 487-504.
[12]	Yangyang MA, Zhaoping ZHONG, Xudong LAI. Enrichment of heavy metals during coal combustion by mineral additives [J]. Chemical Industry and Engineering Progress, 2020, 39(6): 2479-2486.
[13]	Xueli GENG, Ying MENG, Haifeng CONG, Hong LI, Xin GAO, Xingang LI. Review on the synthesis process and industrialization of polyoxymethylene dimethyl ethers [J]. Chemical Industry and Engineering Progress, 2020, 39(12): 4993-5008.
[14]	Mengling DAI, Zhigao SUN, Juan LI, Cuimin LI, Haifeng HUANG. Progress on promotion technology for gas storage in hydrates [J]. Chemical Industry and Engineering Progress, 2020, 39(10): 3975-3986.
[15]	Zhe GONG, Xiaoqin SHANG, Jinchan YANG, Wenjin HUANG, Xinqiao LAI, Dantong LIU, Jionghao HUANG. Synthesis and properties of palmitoyl methionine surfactant [J]. Chemical Industry and Engineering Progress, 2019, 38(02): 1068-1074.