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Engineering >> 2020, Volume 6, Issue 4 doi: 10.1016/j.eng.2020.02.008

Lipase-Catalyzed Synthesis of Sn-2 Palmitate: A Review

a International Joint Research Laboratory for Lipid Nutrition and Safety, Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, School of Food
Science and Technology, Jiangnan University, Wuxi 214122, China
b Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University (BTBU), Beijing 100048, China
c College of Food Science and Technology, Henan University of Technology, Zhengzhou 450001, China
d Wilmar (Shanghai) Biotechnology Research and Development Center Co., Ltd., Shanghai 200137, China
e Department of Food Science and Technology, The University of Georgia, Athens, GA 30602, USA

Received: 2018-08-30 Revised: 2018-10-07 Accepted: 2019-05-08 Available online: 2020-03-05

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Abstract

Human milk fat (HMF) is an important source of nutrients and energy for infants. Triacylglycerols (TAGs) account for about 98% of HMF and have a unique molecular structure. HMF is highly enriched in palmitic acid (PA) at the sn-2 position of the glycerol backbone (more than 70%) and in unsaturated fatty acids at the sn-1,3 position. The specific TAG structure in HMF plays a valuable function in infant growth. Sn-2 palmitate (mainly 1,3-dioleoyl-2-palmitoyl-glycerol) is one of the structured TAGs that is commonly supplemented into infant formula in order to enable it to present a similar structure to HMF. In this review, the development of the lipase-catalyzed synthesis of sn-2 palmitate over the last 25 years are summarized, with a focus on reaction schemes in a laboratory setting. Particular attention is also paid to the commercialized sn-1,3 regioselective lipases that are used in structured TAGs synthesis, to general methods of TAG analysis, and to successfully developed sn-2 palmitate products on the market. Prospects for the lipase-catalyzed synthesis of sn-2 palmitate are discussed.

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References

[ 1 ] Xu X. Production of specific-structured triacylglycerols by lipase-catalyzed reactions: a review. Eur J Lipid Sci Technol 2000;102(4):287–303. link1

[ 2 ] Jensen RG. The lipids in human milk. Prog Lipid Res 1996;35(1):53–92. link1

[ 3 ] Kallio H, Nylund M, Boström P, Yang B. Triacylglycerol regioisomers in human milk resolved with an algorithmic novel electrospray ionization tandem mass spectrometry method. Food Chem 2017;233:351–60. link1

[ 4 ] Zou L, Pande G, Akoh CC. Infant formula fat analogs and human milk fat: new focus on infant developmental needs. Annu Rev Food Sci Technol 2016;7:139–65. link1

[ 5 ] Akoh CC. Handbook of functional lipids. Boca Raton: CRC Press; 2005. link1

[ 6 ] Zou X, Huang J, Jin Q, Guo Z, Liu Y, Cheong L, et al. Lipid composition analysis of milk fats from different mammalian species: potential for use as human milk fat substitutes. J Agric Food Chem 2013;61(29):7070–80. link1

[ 7 ] Yao Y, Zhao G, Xiang J, Zou X, Jin Q, Wang X. Lipid composition and structural characteristics of bovine, caprine and human milk fat globules. Int Dairy J 2016;56:64–73. link1

[ 8 ] Jensen RG. Lipids in human milk. Lipids 1999;34(12):1243–71. link1

[ 9 ] Haddad I, Mozzon M, Strabbioli R, Frega NG. A comparative study of the composition of triacylglycerol molecular species in equine and human milks. Dairy Sci Technol 2012;92(1):37–56. link1

[10] Zhang X, Qi C, Zhang Y, Wei W, Jin Q, Xu Z, et al. Identification and quantification of triacylglycerols in human milk fat using ultra-performance convergence chromatography and quadrupole time-of-flight mass spectrometery with supercritical carbon dioxide as a mobile phase. Food Chem 2019;275:712–20. link1

[11] Mu H, Høy CE. The digestion of dietary triacylglycerols. Prog Lipid Res 2004;43(2):105–33. link1

[12] Innis SM, Dyer R, Quinlan P, Diersen-Schade D. Palmitic acid is absorbed as sn-2 monopalmitin from milk and formula with rearranged triacylglycerols and results in increased plasma triglyceride sn-2 and cholesteryl ester palmitate in piglets. J Nutr 1995;125(1):73–81. link1

[13] Lien EL. The role of fatty acid composition and positional distribution in fat absorption in infants. J Pediatr 1994;125(5 Pt 2):S62–8. link1

[14] Quinlan PT, Lockton S, Irwin J, Lucas AL. The relationship between stool hardness and stool composition in breast- and formula-fed infants. J Pediatr Gastroenterol Nutr 1995;20(1):81–90. link1

[15] Innis SM. Dietary triacylglycerol structure and its role in infant nutrition. Adv Nutr 2011;2(3):275–83. link1

[16] Bar-Yoseph F, Lifshitz Y, Cohen T. Review of sn-2 palmitate oil implications for infant health. Prostaglandins Leukot Essent Fatty Acids 2013;89 (4):139–43. link1

[17] Namal Senanayake SPJ, Shahidi F. Modification of fats and oils via chemical and enzymatic methods. In: Shahidi F, editor. Bailey’s industrial oil and fat products. Hoboken: John Wiley & Sons; 2005. link1

[18] Soumanou MM, Pérignon M, Villeneuve P. Lipase-catalyzed interesterification reactions for human milk fat substitutes production: a review. Eur J Lipid Sci Technol 2013;115(3):270–85. link1

[19] Ferreira-Dias S, Tecelão C. Human milk fat substitutes: advances and constraints of enzyme-catalyzed production. Lipid Technol 2014;26 (8):183–6. link1

[20] Kim BH, Akoh CC. Recent research trends on the enzymatic synthesis of structured lipids. J Food Sci 2015;80(8):C1713–24. link1

[21] Bornscheuer UT. Enzymes in lipid modification: an overview. In: Bornscheuer UT, editor. Lipid modification by enzymes and engineered microbes. Boulder: AOCS Press; 2018. p. 1–9. link1

[22] Macrae AR. Lipase-catalyzed interesterification of oils and fats. J Am Oil Chem Soc 1983;60(2 Pt 1):291–4. link1

[23] Adlercreutz P. Enzyme-catalysed lipid modification. Biotechnol Genet Eng Rev 1994;12(1):231–54. link1

[24] Kovac A, Stadler P, Haalck L, Spener F, Paltauf F. Hydrolysis and esterification of acylglycerols and analogs in aqueous medium catalyzed by microbial lipases. Biochim Biophys Acta 1996;1301(1–2):57–66. link1

[25] Stadler P, Kovac A, Haalck L, Spener F. Paltauf F. Stereoselectivity of microbial lipases. The substitution at position sn-2 of triacylglycerol analogs influences the stereoselectivity of different microbial lipases. Eur J Biochem 1995;227 (1–2):335–43. link1

[26] Pleiss J. Molecular basis of specificity and stereoselectivity of microbial lipases toward triacylglycerols. In: Bornscheuer UT, editor. Enzymes in lipid modification. Berlin: Wiley-VCH Verlag GmbH; 2000. p. 85–99. link1

[27] Villeneuve P, Pina M, Montet D, Graille J. Determination of lipase specificities through the use of chiral triglycerides and their racemics. Chem Phys Lipids 1995;76(1):109–13. link1

[28] Watanabe Y, Nagao T, Shimada Y. Control of the regiospecificity of Candida antarctica lipase by polarity. N Biotechnol 2009;26(1–2):23–8. link1

[29] Bornscheuer UT. Enzymes in lipid modification. Berlin: Wiley-VCH Verlag GmbH; 2000. link1

[30] Adlercreutz P. Immobilisation and application of lipases in organic media. Chem Soc Rev 2013;42(15):6406–36. link1

[31] Bornscheuer UT, Huisman GW, Kazlauskas RJ, Lutz S, Moore JC, Robins K. Engineering the third wave of biocatalysis. Nature 2012;485(7397): 185–94. link1

[32] Nagao T, Shimada Y, Sugihara A, Tominaga Y. Increase in stability of Fusarium heterosporum lipase. J Mol Catal B Enzym 2002;17(3–5):125–32. link1

[33] Eisenmenger MJ, Reyes-De-Corcuera JI. High hydrostatic pressure increased stability and activity of immobilized lipase in hexane. Enzyme Microb Technol 2009;45(2):118–25. link1

[34] Abdul Wahab R, Basri M, Raja Abdul Rahman RNZ, Salleh AB. Abdul Rahman MB, Leow TC. Development of a catalytically stable and efficient lipase through an increase in hydrophobicity of the oxyanion residue. J Mol Catal B Enzym 2015;122:282–8. link1

[35] Mu H, Porsgaard T. The metabolism of structured triacylglycerols. Prog Lipid Res 2005;44(6):430–48. link1

[36] Indelicato S, Bongiorno D, Pitonzo R, Di Stefano V, Calabrese V, Indelicato S, et al. Triacylglycerols in edible oils: determination, characterization, quantitation, chemometric approach and evaluation of adulterations. J Chromatogr A 2017;1515:1–16. link1

[37] Laakso P. Mass spectrometry of triacylglycerols. Eur J Lipid Sci Technol 2002;104(1):43–9. link1

[38] Buchgraber M, Ulberth F, Emons H, Anklam E. Triacylglycerol profiling by using chromatographic techniques. Eur J Lipid Sci Technol 2004;106 (9):621–48. link1

[39] Fuchs B, Süß R, Teuber K, Eibisch M, Schiller J. Lipid analysis by thin-layer chromatography—a review of the current state. J Chromatogr A 2011;1218 (19):2754–74. link1

[40] Ruiz-Samblás C, González-Casado A, Cuadros-Rodríguez L. Triacylglycerols determination by high-temperature gas chromatography in the analysis of vegetable oils and foods: a review of the past 10 years. Crit Rev Food Sci Nutr 2015;55(11):1618–31. link1

[41] Christie WW, Han X. Chromatographic analysis of lipids: general principles. In: Christie WW, Han X, editors. Lipid analysis. Cambridge: Woodhead Publishing Limited; 2012. link1

[42] Zhang X, Nie K, Zheng Y, Wang F, Deng L, Tan T. Lipase Candida sp. 99– 125coupled with b-cyclodextrin as additive synthesized the human milk fat substitutes. J Mol Catal B Enzym 2016;125:1–5. link1

[43] Zou X, Huang J, Jin Q, Guo Z, Cheong L, Xu X, et al. Preparation of human milk fat substitutes from lard by lipase-catalyzed interesterification based on triacylglycerol profiles. J Am Oil Chem Soc 2014;91(12):1987–98. link1

[44] Vyssotski M, Bloor SJ, Lagutin K, Wong H, Williams DBG. Efficient separation and analysis of triacylglycerols: quantitation of b-palmitate (OPO) in oils and infant formulas. J Agric Food Chem 2015;63(26):5985–92. link1

[45] Zheng M, Wang S, Xiang X, Shi J, Huang J, Deng Q, et al. Facile preparation of magnetic carbon nanotubes-immobilized lipase for highly efficient synthesis of 1,3-dioleoyl-2-palmitoylglycerol-rich human milk fat substitutes. Food Chem 2017;228:476–83. link1

[46] He Y, Qiu C, Guo Z, Huang J, Wang M, Chen B. Production of new human milk fat substitutes by enzymatic acidolysis of microalgae oils from Nannochloropsis oculata and Isochrysis galbana. Bioresour Technol 2017;238:129–38. link1

[47] Zou X, Jin Q, Guo Z, Xu X, Wang X. Preparation and characterization of human milk fat substitutes based on triacylglycerol profiles. J Am Oil Chem Soc 2016;93(6):781–92. link1

[48] Zou X, Jin Q, Guo Z, Xu X, Wang X. Preparation of human milk fat substitutes from basa catfish oil: combination of enzymatic acidolysis and modeled blending. Eur J Lipid Sci Technol 2016;118(11):1702–11. link1

[49] Liu C, Zhang Y, Zhang X, Nie K, Deng L, Wang F. The two-step synthesis of 1,3- oleoyl-2-palmitoylglycerol by Candida sp. 99–125 lipase. J Mol Catal B Enzym 2016;133(Supp 1):S1–5. link1

[50] Faustino AR, Osório NM, Tecelão C, Canet A, Valero F, Ferreira-Dias S. Camelina oil as a source of polyunsaturated fatty acids for the production of human milk fat substitutes catalyzed by a heterologous Rhizopus oryzae lipase. Eur J Lipid Sci Technol 2016;118(4):532–44. link1

[51] Zhao XY, Wang XD, Liu X, Zhu WJ, Mei YY, Li WW, et al. Structured lipids enriched with unsaturated fatty acids produced by enzymatic acidolysis of silkworm pupae oil using oleic acid. Eur J Lipid Sci Technol 2015;117 (6):879–89. link1

[52] Álvarez C, Akoh C. Enzymatic synthesis of infant formula fat analog enriched with capric acid. J Am Oil Chem Soc 2015;92(7):1003–14. link1

[53] Cai H, Li Y, Zhao M, Fu G, Lai J, Feng F. Immobilization, regiospecificity characterization and application of Aspergillus oryzae lipase in the enzymatic synthesis of the structured lipid 1,3-dioleoyl-2-palmitoylglycerol. PLoS ONE 2015;10(7):e0133857. link1

[54] Kotani K, Yamamoto Y, Hara S. Enzymatic preparation of human milk fat substitutes and their oxidation stability. J Oleo Sci 2015;64(3):275–81. link1

[55] Lee NK, Oh SW, Kwon DY, Yoon SH. Production of 1,3-dioleoyl-2-palmitoyl glycerol as a human milk fat substitute using enzymatic interesterification of natural fats and oils. Food Sci Biotechnol 2015;24(2):433–7. link1

[56] Liu SL, Dong XY, Wei F, Wang X, Lv X, Zhong J, et al. Ultrasonic pretreatment in lipase-catalyzed synthesis of structured lipids with high 1,3-dioleoyl-2- palmitoylglycerol content. Ultrason Sonochem 2015;23:100–8. link1

[57] Wang X, Zou W, Sun X, Zhang Y, Wei L, Jin Q, et al. Chemoenzymatic synthesis of 1,3-dioleoyl-2-palmitoylglycerol. Biotechnol Lett 2015;37 (3):691–6. link1

[58] Zou X, Jin Q, Guo Z, Huang J, Xu X, Wang X. Preparation of 1,3-dioleoyl-2- palmitoylglycerol-rich structured lipids from basa catfish oil: combination of fractionation and enzymatic acidolysis. Eur J Lipid Sci Technol 2016;118 (5):708–15. link1

[59] Wei W, Feng Y, Zhang X, Cao X, Feng F. Synthesis of structured lipid 1,3- dioleoyl-2-palmitoylglycerol in both solvent and solvent-free system. Lebensm Wiss Technol 2015;60(2):1187–94. link1

[60] Qin XL, Zhong JF, Wang YH, Yang B, Lan DM, Wang FH. 1,3-dioleoyl-2- palmitoylglycerol-rich human milk fat substitutes: production, purification, characterization and modeling of the formulation. Eur J Lipid Sci Technol 2014;116(3):282–90. link1

[61] Li R, Pande G, Sabir JSM, Baeshen NA, Akoh CC. Enrichment of refined olive oil with palmitic and docosahexaenoic acids to produce a human milk fat analogue. J Am Oil Chem Soc 2014;91(8):1377–85. link1

[62] Zou XG, Hu JN, Zhao ML, Zhu XM, Li HY, Liu XR, et al. Lipozyme RM IMcatalyzed acidolysis of Cinnamomum camphora seed oil with oleic acid to produce human milk fat substitutes enriched in medium-chain fatty acids. J Agric Food Chem 2014;62(43):10594–603. link1

[63] Pande G, Sabir JM, Baeshen N, Akoh C. Synthesis of infant formula fat analogs enriched with DHA from extra virgin olive oil and tripalmitin. J Am Oil Chem Soc 2013;90(9):1311–8. link1

[64] Turan D, Yesilçubuk NS, Akoh CC. Enrichment of sn-2 position of hazelnut oil with palmitic acid: optimization by response surface methodology. Lebensm Wiss Technol 2013;50(2):766–72. link1

[65] Pande G, Sabir JSM, Baeshen NA, Akoh CC. Enzymatic synthesis of extra virgin olive oil based infant formula fat analogues containing ARA and DHA: onestage and two-stage syntheses. J Agric Food Chem 2013;61(44):10590–8. link1

[66] Turan D, Sahin Yesilçubuk N, Akoh CC. Production of human milk fat analogue containing docosahexaenoic and arachidonic acids. J Agric Food Chem 2012;60(17):4402–7. link1

[67] Tecelão C, Rivera I, Sandoval G, Ferreira-Dias S. Carica papaya latex: a low-cost biocatalyst for human milk fat substitutes production. Eur J Lipid Sci Technol 2012;114(3):266–76. link1

[68] Yüksel A, Sahin Yesilçubuk N. Enzymatic production of human milk fat analogues containing stearidonic acid and optimization of reactions by response surface methodology. Lebensm Wiss Technol 2012;46(1):210–6. link1

[69] Zou X, Huang J, Jin Q, Liu Y, Song Z, Wang X. Lipase-catalyzed synthesis of human milk fat substitutes from palm stearin in a continuous packed bed reactor. J Am Oil Chem Soc 2012;89(8):1463–72. link1

[70] Cheong LZ, Xu X. Lard-based fats healthier than lard: enzymatic synthesis, physicochemical properties and applications. Lipid Technol 2011;23(1):6–9. link1

[71] da Silva RC, Soares FASDM, Fernandes TG, Castells ALD, da Silva KCG, Gonçalves MIA, et al. Interesterification of lard and soybean oil blends catalyzed by immobilized lipase in a continuous packed bed reactor. J Am Oil Chem Soc 2011;88(12):1925–33. link1

[72] Esteban L, Jimenez MJ, Hita E, Gonzalez PA, Martin L, Robles A. Production of structured triacylglycerols rich in palmitic acid at sn-2 position and oleic acid at sn-1,3 positions as human milk fat substitutes by enzymatic acidolysis. Biochem Eng J 2011;54(1):62–9. link1

[73] Ilyasoglu H, Gultekin-Ozguven M, Ozcelik B. Production of human milk fat substitute with medium-chain fatty acids by lipase-catalyzed acidolysis: optimization by response surface methodology. Lebensm Wiss Technol 2011;44(4):999–1004. link1

[74] Qin XL, Wang YM, Wang YH, Huang HH, Yang B. Preparation and characterization of 1,3-dioleoyl-2-palmitoylglycerol. J Agric Food Chem 2011;59(10):5714–9. link1

[75] Zou XQ, Huang JH, Jin QZ, Liu YF, Song ZH, Wang XG. Lipase-catalyzed preparation of human milk fat substitutes from palm stearin in a solvent-free system. J Agricult Food Chem 2011;59(11):6055–63. link1

[76] Jiménez MJ, Esteban L, Robles A, Hita E, González PA, Muñío MM, et al. Production of triacylglycerols rich in palmitic acid at position 2 as intermediates for the synthesis of human milk fat substitutes by enzymatic acidolysis. Process Biochem 2010;45(3):407–14. link1

[77] Lee JH, Son JM, Akoh CC, Kim MR, Lee KT. Optimized synthesis of 1,3-dioleoyl- 2-palmitoylglycerol-rich triacylglycerol via interesterification catalyzed by a lipase from Thermomyces lanuginosus. N Biotechnol 2010;27(1):38–45. link1

[78] Tecelão C, Silva J, Dubreucq E, Ribeiro MH, Ferreira-Dias S. Production of human milk fat substitutes enriched in omega-3 polyunsaturated fatty acids using immobilized commercial lipases and Candida parapsilosis lipase/ acyltransferase. J Mol Catal, B Enzym 2010;65(1–4):122–7. link1

[79] Wang YH, Qin XL, Zhu QS, Zhou R, Yang B, Li L. Lipase-catalyzed acidolysis of lard for the production of human milk fat substitute. Eur Food Res Technol 2010;230(5):769–77. link1

[80] Pina-Rodriguez AM, Akoh CC. Enrichment of amaranth oil with ethyl palmitate at the sn-2 position by chemical and enzymatic synthesis. J Agric Food Chem 2009;57(11):4657–62. link1

[81] Guncheva M, Zhiryakova D, Radchenkova N, Kambourova M. Acidolysis of tripalmitin with oleic acid catalyzed by a newly isolated thermostable lipase. J Am Oil Chem Soc 2008;85(2):129–32. link1

[82] Maduko CO, Akoh CC, Park YW. Enzymatic production of infant milk fat analogs containing palmitic acid: optimization of reactions by response surface methodology. J Dairy Sci 2007;90(5):2147–54. link1

[83] Nielsen NS, Yang T, Xu X, Jacobsen C. Production and oxidative stability of a human milk fat substitute produced from lard by enzyme technology in a pilot packed-bed reactor. Food Chem 2006;94(1):53–60. link1

[84] Sahín N, Akoh CC, Karaalí A. Human milk fat substitutes containing omega-3 fatty acids. J Agric Food Chem 2006;54(10):3717–22. link1

[85] Srivastava A, Akoh CC, Chang SW, Lee GC, Shaw JF. Candida rugosa lipase LIP1- catalyzed transesterification to produce human milk fat substitute. J Agric Food Chem 2006;54(14):5175–81. link1

[86] Sahin N, Akoh C, Karaali A. Enzymatic production of human milk fat substitutes containing c-linolenic acid: optimization of reactions by response surface methodology. J Am Oil Chem Soc 2005;82(8):549–57. link1

[87] Sahin N, Akoh CC, Karaali A. Lipase-catalyzed acidolysis of tripalmitin with hazelnut oil fatty acids and stearic acid to produce human milk fat substitutes. J Agric Food Chem 2005;53(14):5779–83. link1

[88] Chen ML, Vali SR, Lin JY, Ju YH. Synthesis of the structured lipid 1,3-dioleoyl- 2-palmitoylglycerol from palm oil. J Am Oil Chem Soc 2004;81(6):525–32. link1

[89] Yang T, Xu X, He C, Li L. Lipase-catalyzed modification of lard to produce human milk fat substitutes. Food Chem 2003;80(4):473–81. link1

[90] Nagao T, Shimada Y, Sugihara A, Murata A, Komemushi S, Tominaga Y. Use of thermostable Fusarium heterosporum lipase for production of structured lipid containing oleic and palmitic acids in organic solvent-free system. J Am Oil Chem Soc 2001;78(2):167–72. link1

[91] Shimada Y, Nagao T, Hamasaki Y, Akimoto K, Sugihara A, Fujikawa S, et al. Enzymatic synthesis of structured lipid containing arachidonic and palmitic acids. J Am Oil Chem Soc 2000;77(1):89–93. link1

[92] Schmid U, Bornscheuer UT, Soumanou MM, McNeill GP, Schmid RD. Highly selective synthesis of 1,3-oleoyl-2-palmitoylglycerol by lipase catalysis. Biotechnol Bioeng 1999;64(6):678–84. link1

[93] Mukherjee KD, Kiewitt I. Structured triacylglycerols resembling human milk fat by transesterification catalyzed by papaya (Carica papaya) latex. Biotechnol Lett 1998;20(6):613–6. link1

[94] Schmid U, Bornscheuer U, Soumanou M, McNeill G, Schmid R. Optimization of the reaction conditions in the lipase-catalyzed synthesis of structured triglycerides. J Am Oil Chem Soc 1998;75(11):1527–31. link1

[95] Balcão VM, Malcata FX. Lipase-catalyzed modification of butterfat via acidolysis with oleic acid. J Mol Catal B Enzym 1997;3(1–4):161–9. link1

[96] Lísa M, Velínská H, Holcˇapek M. Regioisomeric characterization of triacylglycerols using silver-ion HPLC/MS and randomization synthesis of standards. Anal Chem 2009;81(10):3903–10. link1

[97] Fraga CG, Prazen BJ, Synovec RE. Comprehensive two-dimensional gas chromatography and chemometrics for the high-speed quantitative analysis of aromatic isomers in a jet fuel using the standard addition method and an objective retention time alignment algorithm. Anal Chem 2000;72(17):4154–62. link1

[98] Holcˇapek M, Dvorˇáková H, Lísa M, Girón AJ, Sandra P, Cvacˇka J. Regioisomeric analysis of triacylglycerols using silver-ion liquid chromatography– atmospheric pressure chemical ionization mass spectrometry: comparison of five different mass analyzers. J Chromatogr A 2010;1217(52):8186–94. link1

[99] Zou XQ, Huang JH, Jin QZ, Guo Z, Liu YF, Cheong LZ, et al. Model for human milk fat substitute evaluation based on triacylglycerol composition profile. J Agric Food Chem 2013;61(1):167–75. link1

[100] Smith KW. Structured triacylglycerols: properties and processing for use in food. In: Talbot G, editor. Specialty oils and fats in food and nutrition. London: Woodhead Publishing; 2015. p. 207–18. link1

[101] Ferreira ML, Tonetto GM. Examples of successful industrial synthesis of structured diglycerides and triglycerides, enzymatic synthesis of structured triglycerides. In: Ferreira ML, Tonetto GM, editors. Enzymatic synthesis of structured triglycerides from laboratory to industry. Berlin: Springer International Publishing; 2017. p. 73–9. link1

[102] Kurvinen JP, Sjövall O, Kallio H. Molecular weight distribution and regioisomeric structure of triacylglycerols in some common human milk substitutes. J Am Oil Chem Soc 2002;79(1):13–22. link1

[103] Happe RP, Gambelli L. Infant formula. In: Talbot G, editor. Specialty oils and fats in food and nutrition. London: Woodhead Publishing; 2015. p. 285–315. link1

[104] Yan Y, Wang Z, Wang X, Wang Y, Xiang J, Kothapalli KSD, et al. Branched chain fatty acids positional distribution in human milk fat and common human food fats and uptake in human intestinal cells. J Funct Foods 2017;29:172–7. link1

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