A Study of Tyrosine O-Phosphorylation via Atherton-Todd Reaction

Abstract

Abstract: The tyrosine Ophosphorylation via AthertonTodd reaction, which was a classical reaction for phosphorylation amines, was first studied in this paper. Reaction of BocTyrOCH₃, which was selected as model substrate, with three dialkyl Hphosphonate diester in the presence of CCl4 and triethylamine produced the corresponding tyrosine Ophosphorylation products in a high yield(over 80). The reaction was conducted in anhydrous THFsolution and monitored by ³¹P NMRand TLC. Then reaction of BocTyrOCH₃ with a complicated Hphosphonate diester, O-3'-acetylthymidin-5'-yl Oisopropyl Hphosphonate diester, also gave a good result and this would be an alternative approach for the synthesis of nucleotide Otyrosine (or tyrosine containing peptide) conjugate. Further, the successful Ophosphoration of three tyrosine containing protected dipeptides, BocTyrValOCH₃, BocAlaTyrOCH₃, BocTyrTyrOCH₃, with diisopropyl Hphosphonate diester demonstrated the effectiveness of the method.

Key words: AthertonTodd reaction, Dialkyl Hphosphonate diester, Tyrosine Ophosphorylation

CLC Number:

O624

TrendMD:

ZHAO Gang, LI YanMei, LUO ShiZhong, HAN Bo, ZHAO YuFen. A Study of Tyrosine O-Phosphorylation via Atherton-Todd Reaction[J]. Chem. J. Chinese Universities, 2001, 22(12): 2034.

[1]	WANG Lu-Yao, GAO Yong, YANG Bing-Qin, SHI Zhen. Synthesis,Structure and Bioactivity of Nitrobenzoimidazole Derivatives [J]. Chem. J. Chinese Universities, 2005, 26(12): 2241.
[2]	AN De-Lie, YANG Shao-Hui, ZHANG Zhi-Yang, PENG Zhi-Hong, ZHANG Ying-Jun, LIU Hong-Ling. Synthesis of Novel Enantiomers Cyclophanes Using 2,2'-Diethynyl-1,1'-binaphthyls as a Structural Block and Their Optical Properties [J]. Chem. J. Chinese Universities, 2005, 26(7): 1268.
[3]	WANG Qiu-An, LUO Jun-Xia, LIAO Tou-Gen. A Novel Synthesis of Optically Pure trans-(+)-Sobrerol [J]. Chem. J. Chinese Universities, 2004, 25(6): 1069.
[4]	AN De-Lie, TAN Xiao-Hua, PENG Zhi-Hong, SHAO Guang . Preparation of dl-Dibenzophenanthrene by Using Benzyl-type Binaphthyl Disulfone [J]. Chem. J. Chinese Universities, 2003, 24(12): 2218.
[5]	Hasiqimuge, LI Song-Bo, XU Ai-Ju, Guoxingbatu. New Method for Preparing Zeolites Matrix Nanometer Noncrystal Soft Magnetic Materials and Their Magnetism [J]. Chem. J. Chinese Universities, 2003, 24(9): 1633.
[6]	HU Wei-Xiao, SUN Ya-Quan, YUAN Qing, YANG Zhong-Yu. Catalytical Rearrangement of 1,6-Dihydro-S-tetrazine with Isocyanate [J]. Chem. J. Chinese Universities, 2002, 23(10): 1877.
[7]	CAO Wei-Guo, DING Wei-Yu, WANG Li-Yan, SONG Li-Ping, ZHANG Qian-Ying. Chemistry and Applications of Phosphonium and Arsonium Ylides(ⅩⅩⅨ)──Studies on the Hydrolysis of Arsonium Ylides Containing Perfluoroalkyl Group andSynthesis of₂-Pyranone Derivatives [J]. Chem. J. Chinese Universities, 2002, 23(5): 839.
[8]	HE Hong-Yun, PANG Wen-Qin, LIU Wu-Yang, DENG Feng . Influence of the Synthesis Condition on the Crystallization of Fe-β Zeolite Molecular Sieves in the Absence of Aluminum [J]. Chem. J. Chinese Universities, 2002, 23(3): 353.
[9]	WANG Zhi-Yong, ZHANG Zu-De, LI Qian-Rong, GUO Qing-Xiang . A Novel Method for the Syntheses of Stibazole Compounds [J]. Chem. J. Chinese Universities, 2002, 23(1): 58.
[10]	LIU Da-Xue, WANG Quan, ZHANG Li-Chen, DA Chao-Shan, WANG Rui . Trimethylsilylcyanation of Aromatic Aldehydes Catalyzed by BINOL-Li Salt [J]. Chem. J. Chinese Universities, 2001, 22(4): 601.
[11]	CAO Wei-Guo, DING Wei-Yu, TONG Wei-Qi, LIU Xin, QIU Meng-Yao . Studies on the Reaction of 1,2,3-Trisubstituted Electron-deficient Cyclopropane Derivatives with Methanol [J]. Chem. J. Chinese Universities, 2000, 21(5): 740.
[12]	ZHANG Zhe, ZHOU Gang, GAO Xiao-Lei, LI Yu-Lin, LIAO Ren-An. Asymmetric Synthesis of 7-epi-γ-Eudesmol [J]. Chem. J. Chinese Universities, 2000, 21(4): 573.
[13]	LI Run-Tao, GE Ze-Mei, CHENG Tie-Ming, CAI Meng-Shen . New Synthetic Method for Dithiocarbamates [J]. Chem. J. Chinese Universities, 1999, 20(12): 1897.
[14]	YANG Guang-Fu, LIU Hua-Yin, YANG Hua-Zheng . Acidity Constants of Herbicidal Sulfonylureas and Sulfonamides from Potentiometric Determinations in Aqueous Dimethyl Sulfoxide [J]. Chem. J. Chinese Universities, 1999, 20(12): 1883.
[15]	CHEN Hong, DAI Zhi-Qun, QU Fan-Qi, HUANG Xiao-Ling . Synthesis of Glucosyl Esters of N,N-Di[O-nitrophenylamino)ethyl]glycine [J]. Chem. J. Chinese Universities, 1999, 20(11): 1725.

A Study of Tyrosine O-Phosphorylation via Atherton-Todd Reaction

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments