Novel synthesis of steryl esteryl esters from β-sitosterol and N-phosphoryl amino acid under microwave irradiation

GRAPHICAL ABSTRACT ABSTRACT Ten novel N-phosphoryl amino acids β-sitosterol esters were synthesized by coupling the N-phosphoryl amino acids with β-sitosterol under microwave irradiation, and their structures were elucidated by IR, NMR, and HR MS. Various reaction conditions including the catalyst, solvent, temperature and time were investigated. Under the optimal conditions, the reaction was finished in 20 min with 60–87% yields by employing DCC/DMAP as a catalyst system at room temperature.

[1]  L. Pan,et al.  Novel synthesis of steryl esters from phytosterols and amino Acid. , 2011, Journal of agricultural and food chemistry.

[2]  Yufen Zhao,et al.  Intermolecular Phosphoryl Transfer of N-Phosphoryl Amino Acids , 2011 .

[3]  N. Farshori,et al.  DCC/DMAP mediated esterification of hydroxy and non-hydroxy olefinic fatty acids with β-sitosterol: In vitro antimicrobial activity , 2010 .

[4]  U. Laufs,et al.  Controversial role of plant sterol esters in the management of hypercholesterolaemia , 2008, European heart journal.

[5]  J. Gomes,et al.  Androstenedione production by biotransformation of phytosterols. , 2008, Bioresource technology.

[6]  Xiaolan Chen,et al.  Synthesis of Phosphoryl Amino Acids Chrysin Esters , 2008 .

[7]  R. Mensink,et al.  Plant stanol and sterol esters in the control of blood cholesterol levels: mechanism and safety aspects. , 2005, The American journal of cardiology.

[8]  Y. F. Zhao,et al.  N-Phosphoryl Amino Acids and Biomolecular Origins. Review Paper in Honor of the 50th Anniversary of the Publication of ``A Production of Amino Acids under Possible Primitive Earth Conditions'' (Miller, 1953) , 2004, Origins of life and evolution of the biosphere.

[9]  Soon-Seok Hong,et al.  Effect of a New β-Sitosterol Analogue on Plasma Lipid Concentrations in Rats , 2004 .

[10]  Ki-Teak Lee,et al.  Lipase-catalyzed production of phytosteryl esters and their crystallization behavior in corn oil , 2004 .

[11]  H. Fu,et al.  Synthesis, In Vitro Anticancer Evaluation, and Interference with Cell Cycle Progression of N‐Phosphoamino Acid Esters of Zidovudine and Stavudine , 2004, Nucleosides, nucleotides & nucleic acids.

[12]  B. Folmer Sterol surfactants: from synthesis to applications. , 2003, Advances in colloid and interface science.

[13]  G. Courtois,et al.  Solid base catalysts for the synthesis of phytosterol esters , 2003 .

[14]  N. Weber,et al.  Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst. , 2001, Journal of agricultural and food chemistry.

[15]  Y. Shimada,et al.  Enzymatic synthesis of steryl esters of polyunsaturated fatty acids , 1999 .

[16]  J. Weststrate,et al.  Plant sterol-enriched margarines and reduction of plasma total- and LDL-cholesterol concentrations in normocholesterolaemic and mildly hypercholesterolaemic subjects , 1998, European Journal of Clinical Nutrition.

[17]  P. J. Jones,et al.  Dietary phytosterols as cholesterol-lowering agents in humans. , 1997, Canadian journal of physiology and pharmacology.

[18]  Q. Yan,et al.  KINETICS OF PHOSPHORYL TRANSFER REACTIONS OF PHOSPHOAMINO ACIDS AND ESTERS IN THE PRESENCE OF IMIDAZOLE , 1995 .

[19]  Marian Mikoz.xl,et al.  Recent developments in the carbodiimide chemistry , 1981 .