Synthesis and Application of β-Thiolated Amino Acids

doi:10.6023/cjoc202303023

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3089-3097.DOI: 10.6023/cjoc202303023 Previous Articles Next Articles

β-巯基氨基酸的合成与应用

上官豪若^a, 黄平^b, 戴振亚^a^,^*(), 王平^b^,^*()

a 中国药科大学药学院江苏南京 211100
b 上海交通大学化学化工学院上海市手性药物分子工程重点实验室上海 200240

收稿日期:2023-03-16 修回日期:2023-04-23 发布日期:2023-05-11
基金资助:
国家自然科学基金(22077080)

Synthesis and Application of β-Thiolated Amino Acids

Haoruo Shangguan^a, Ping Huang^b, Zhenya Dai^a(), Ping Wang^b()

a School of Pharmacy, China Pharmaceutical University, Nanjing, Jiangsu 211100
b Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2023-03-16 Revised:2023-04-23 Published:2023-05-11
Contact: * E-mail: daizhenya@hotmail.com;wangp1@sjtu.edu.cn
Supported by:
National Natural Science Foundation of China(22077080)

Native chemical ligation (NCL) is a milestone reaction in protein chemical synthesis. The NCL involves a reaction between an unprotected peptide with C-terminal thioester and a second unprotected peptide with N-terminal cysteine, which could give a new peptide in a neutral aqueous buffer solution. The cysteine abundance of natural proteins is only 1.7%, which makes it difficult to find suitable cysteine reaction sites and hinders the widespread application of NCL. The “NCL-desulfuri- zation” strategy extended the ligation site to alanine, inspiring chemists to mediate NCL reactions through different types of β-thiolated amino acids. After the NCL is completed, native peptide can be obtained through desulfurization reactions. The “NCL-desulfurization” provides more options for protein synthesis. In recent years, several research groups have completed the synthesis of β-thiolated phenylalanine, leucine, arginine, aspartic acid, asparagine, lysine, methionine, tryptophan, glutamic acid and glutamine, and applied NCL-desulfurization strategy to synthesize proteins. In this article, the synthesis and application of the above β-thiolated amino acids are reviewed.

Key words: native chemical ligation (NCL), β-thiolated amino acids, desulfurization

Cite this article

Haoruo Shangguan, Ping Huang, Zhenya Dai, Ping Wang. Synthesis and Application of β-Thiolated Amino Acids[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3089-3097.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 13

Scheme 1. Reaction of NCL-desulfurization

Scheme 2. Synthesis of β-thiolated phenylalanine 7

Scheme 3. Synthesis of β-thiolated phenylalanine 13

Scheme 4. Synthesis of β-thiolated leucine 20

Scheme 5. Synthesis of β-thiolated leucine 27

Scheme 6. Synthesis of β-thiolated arginine 37

Scheme 7. Synthesis of β-thiolated asparticacid 44

Scheme 8. Synthesis of β-thiolated asparticacid 52

Scheme 9. Synthesis of β-thiolated asparagine 59 and 60

Scheme 10. Synthesis of β-thiolated lysine 67 and 68

Scheme 11. Mechanism of photocatalyis Giese reaction

Scheme 12. Different types of β-thiolated amino acids

Scheme 13. Synthesis of β-thiolated aryl amino acids

References 46

[1]	Dawson P. E.; Muir T. W.; Clark-Lewis I.; Kent S. B. H. Science 1994, 266, 776. pmid: 7973629
[2]	McCaldon P.; Argos P. Proteins 1988, 4, 99. pmid: 3227018
[3]	Yan L. Z.; Dawson P. E. J. Am. Chem. Soc. 2001, 123, 526. pmid: 11456564
[4]	Wan Q.; Danishefsky S. J. Angew. Chem., Int. Ed. 2007, 46, 9248. doi: 10.1002/(ISSN)1521-3773
[5]	Guan I.; Williams K.; Liu J. S. T.; Liu X.-Y. Front. Chem. 2022, 9, 826764. doi: 10.3389/fchem.2021.826764
[6]	Wong C. T. T.; Tung C.-L.; Li X.-C. Mol. BioSyst. 2013, 9, 826. doi: 10.1039/c2mb25437a
[7]	He Q.-Q.; Fang G.-M.; Liu L. Chin. Chem. Lett. 2013, 24, 265. doi: 10.1016/j.cclet.2013.03.013
[8]	Wang S.-Y.; Thopate Y. A.; Zhou Q.-Q.; Wang P. Chin. J. Chem. 2019, 37, 1181. doi: 10.1002/cjoc.v37.11
[9]	Morishita Y.; Kaino T.; Okamoto R.; Izumi M.; Kajihara Y. Tetrahedron Lett. 2015, 56, 6565.
[10]	Tam J. P.; Yu Q.-T. Biopolymers 1998, 46, 319. pmid: 9754028
[11]	Easton C. J.; Hutton C. A.; Tan E. W.; Tiekink E. R. T. Tetrahedron Lett. 1990, 31, 7059. doi: 10.1016/S0040-4039(00)97242-3
[12]	Crich D.; Banerjee A. J. Org. Chem. 2006, 71, 7106. doi: 10.1021/jo061159i
[13]	Crich D.; Banerjee A. J. Am. Chem. Soc. 2007, 129, 10064. doi: 10.1021/ja072804l
[14]	Merrifield R. B. J. Am. Chem. Soc. 1963, 85, 2149. doi: 10.1021/ja00897a025
[15]	Back T. G.; Baron D. L.; Yang K.-X. J. Org. Chem. 1993, 58, 2407. doi: 10.1021/jo00061a011
[16]	Malins L. R.; Giltrap A. M.; Dowman L. J.; Payne R. J. Org. Lett. 2015, 17, 2070. doi: 10.1021/acs.orglett.5b00597 pmid: 25860301
[17]	Passiniemi M.; Koskinen A. M. Beilstein J. Org. Chem. 2013, 9, 2641. doi: 10.3762/bjoc.9.300 pmid: 24367429
[18]	Thompson R. E.; Liu X.-Y.; Alonso-Garcia N.; Pereira P. J. B.; Jolliffe K. A.; Payne R. J. J. Am. Chem. Soc. 2014, 136, 8161. doi: 10.1021/ja502806r pmid: 24873761
[19]	Mirabeau O.; Perlas E.; Severini C.; Audero E.; Gascuel O.; Possenti R.; Birney E.; Rosenthal N.; Gross C. Genome Res. 2007, 17, 320. doi: 10.1101/gr.5755407 pmid: 17284679
[20]	Narayan R. S.; VanNieuwenhze M. S. Org. Lett. 2005, 7, 2655. pmid: 15957914
[21]	Harpaz Z.; Siman P.; Kumar K. S. A.; Brik A. ChemBioChem 2010, 11, 1232. doi: 10.1002/cbic.201000168 pmid: 20437446
[22]	Hetzer C.; Dormeyer W.; Schnolzer M.; Ott M. Microbes Infect. 2005, 7, 1364. doi: 10.1016/j.micinf.2005.06.003
[23]	Tan Z.-P.; Shang S.-Y.; Danishefsky S. J. Angew. Chem., Int. Ed. 2010, 49, 9500. doi: 10.1002/anie.201005513
[24]	Malins L. R.; Cergol K. M.; Payne R. J. ChemBioChem 2013, 14, 559. doi: 10.1002/cbic.201300049 pmid: 23426906
[25]	Garner P.; Park J. M. J. Org. Chem. 1987, 52, 2361. doi: 10.1021/jo00388a004
[26]	Huang H.; Greenberg M. M. J. Org. Chem. 2008, 73, 2695. doi: 10.1021/jo702614p
[27]	Chen X.; Tureček F. J. Am. Chem. Soc. 2006, 128, 12520. doi: 10.1021/ja063676o
[28]	Thompson R. E.; Chan B.; Radom L.; Jolliffe K. A.; Payne R. J. Angew. Chem., Int. Ed. 2013, 52, 9723. doi: 10.1002/anie.201304793 pmid: 23893778
[29]	Shibata N.; Baldwin J. E.; Jacobs A.; Wood M. E. Tetrahedron Lett. 1996, 52, 12839. doi: 10.1016/0040-4020(96)00765-X
[30]	Hauptmann H.; Berl H. J. Am. Chem. Soc. 1955, 77, 704. doi: 10.1021/ja01608a047
[31]	Guan X.-Y.; Drake M. R.; Tan Z.-P. Org. Lett. 2013, 15, 6128. doi: 10.1021/ol402984r
[32]	Nonaka N.; Farr S. A.; Kageyama H.; Shioda S.; Banks W. A. J. Pharmacol. Exp. Ther 2008, 325, 513. doi: 10.1124/jpet.107.132381 pmid: 18270319
[33]	Sayers J.; Thompson R. E.; Perry K. J.; Malins L. R.; Payne R. J. Org. Lett. 2015, 17, 4902. doi: 10.1021/acs.orglett.5b02468
[34]	Dao Y.-K.; Han L.; Wang H.-X.; Dong S.-W. Org. Lett. 2019, 21, 3265. doi: 10.1021/acs.orglett.9b00980
[35]	Zhang X.; King-Smith E.; Renata H. Angew. Chem., Int. Ed. 2018, 57, 5037. doi: 10.1002/anie.201801165 pmid: 29481729
[36]	Pan Y. C.; Stern A. S.; Familletti P. C.; Khan F. R.; Chizzonite R. Eur. J. Biochem. 1987, 166, 145. pmid: 3109913
[37]	Yin H.-L.; Zheng M.-J.; Chen H.; Wang S.-Y.; Zhou Q.-Q.; Zhang Q.; Wang P. J. Am. Chem. Soc. 2020, 142, 14201. doi: 10.1021/jacs.0c04994
[38]	Jeanguenat A.; Seebach D. J. Chem. Soc., Perkin Trans. 1 1991, 2291.
[39]	Zheng M.-J.; Yin H.-L.; Wang S.-Y.; Wang P. Synthesis 2022, 54, 4592. doi: 10.1055/a-1874-4829
[40]	Li H.-X.; Zhang J.; An C.; Dong S.-W. J. Am. Chem. Soc. 2021, 143, 2846. doi: 10.1021/jacs.0c12448
[41]	Zhao J.; Liu J.-Z.; Liu X.-L.; Ye F.-R.; Wang S.-Y.; Wang P. Tetrahedron Lett. 2022, 104, 154024. doi: 10.1016/j.tetlet.2022.154024
[42]	Wang S.-Y.; Zhou Q.-Q.; Li Y.-X.; Wei B.-C.; Liu X.-L.; Zhao J.; Ye F.-R.; Zhou Z. N.; Ding B.; Wang P. J. Am. Chem. Soc. 2022, 144, 1232. doi: 10.1021/jacs.1c10324
[43]	Sun Z.-Q.; Li X.-C. Chin. J. Chem. 2021, 39, 2795. doi: 10.1002/cjoc.v39.10
[44]	Li Y.-X.; Liu J.-Z.; Zhou Q.-Q.; Zhao J.; Wang P. Chin. J. Chem. 2021, 39, 1861. doi: 10.1002/cjoc.v39.7
[45]	Dao Y.-K.; Wang B.; Dong W.-D.; Zhang J.; Zhong C.; Zhang Z.-L.; Dong S.-W. Chin. J. Chem. 2021, 39, 2509. doi: 10.1002/cjoc.v39.9
[46]	Chen Y.; Qin W.; Wang C. Chin. J. Chem. 2022, 40, 628. doi: 10.1002/cjoc.v40.5

β-巯基氨基酸的合成与应用

Synthesis and Application of β-Thiolated Amino Acids

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 13

References 46

Related Articles 6

Recommended Articles

Metrics

Comments

[1]	Guan Chaojian, Wang Tao, Wang Jun, Li Yiming. Synthesis of Post-translational Modifier Protein NEDD8 via Ligation of Peptide Hydrazides [J]. Chin. J. Org. Chem., 2016, 36(11): 2763-2768.
[2]	Zhao Dishun, Li Junpan, Zhang Juan, Ren Peibing, Ge Jingjing, Ren Tengjie, Cui Yun. Extractive Desulfurization of Fuel Oil with Metal-Based Hyamine Ionic Liquids [J]. Chin. J. Org. Chem., 2014, 34(7): 1462-1468.
[3]	PANUNZIO Mauro^,a, BANDINI Elisa^b, D'AURIZIO An-tonio^b, MARTELLI Giorgio^b TAMANINI Emili-ano^b, XIAO Shang-You^c, XIA Zhi-Ning^,c. Microwave-Assisted Desulfurization of Significant Biologically Active Compounds by Raney Nickel [J]. Chin. J. Org. Chem., 2008, 28(01): 60-64.
[4]	Li Yan;Chen Zuxing;Shi Congyun. Synthesis of S-(+)-sulcatol by enzymatic reduction of β - ketosulfone [J]. Chin. J. Org. Chem., 2000, 20(3): 388-390.
[5]	LI YAN;HUANG JINXIA;FANG GUOSU;CHEN ZUXING;XU ZHANGHUANG. Bornanesultam-directed synthesis of (S) and (R) the alarm pheromone of the leaf-cutting ant [J]. Chin. J. Org. Chem., 1997, 17(5): 438-441.
[6]	LI YAN;XU ZHANGHUANG;HUANG JINXIA;CHEN ZUXING;GAO MINGZHANG. Synthesis of (+)-sucatol using a chiral sulfoxide [J]. Chin. J. Org. Chem., 1995, 15(5): 542-545.