Stereoselective Synthesis of β-Thiolated Aryl Amino Acids

Abstract

A variety of β-thiolated aryl amino acids were readily synthesized in moderate to excellent yields via 1,4-addition from a readily-accessible thiazoline precursor, which can be prepared from cysteine methyl ester hydrochloride in just three steps. The thiolated products can be subsequently deprotected within one single step in high yields and used directly for subsequent solid-phase peptide synthesis.

Key words

β-thiolated amino acids - Giese reaction - Michael reaction - cysteine surrogates - native chemical ligation

Publication History

Received: 15 May 2022

Accepted after revision: 13 June 2022

Accepted Manuscript online:
13 June 2022

Article published online:
20 July 2022

• References

• 1a Mamathambika BS, Bardwell JC. Annu. Rev. Cell Dev. Biol. 2008; 24: 211
• 1b Jacob C, Giles GI, Giles NM, Sies H. Angew. Chem. Int. Ed. 2003; 42: 4742
• 1c Zhang R, Genov M, Pretsch A, Pretsch D, Moloney MG. Chem. Sci. 2021; 12: 16106
• 2a Paulsen CE, Carroll KS. Chem. Rev. 2013; 113: 4633
• 2b Hartle MD, Pluth MD. Chem. Soc. Rev. 2016; 45: 6108
• 3a Jacob C, Giles GI, Giles NM, Sies H. Angew. Chem. Int. Ed. 2003; 42: 4742
• 3b Marino SM, Gladyshev VN. J. Mol. Biol. 2010; 404: 902
• 3c Fass D, Thorpe C. Chem. Rev. 2018; 118: 1169
• 4a Davie EA. C, Mennen SM, Xu Y, Miller SJ. Chem. Rev. 2007; 107: 5759
• 4b Hruby VJ. Acc. Chem. Res. 2001; 34: 389
• 5a Bondalapati S, Jbara M, Brik A. Nat. Chem. 2016; 8: 407
• 5b Dawson Philip E, Muir Tom W, Clark-Lewis I, Kent Stephen BH. Science 1994; 266: 776
• 5c Ye F, Zhao J, Xu P, Liu X, Yu J, Shangguan W, Liu J, Luo X, Li C, Ying T, Wang J, Yu B, Wang P. Angew. Chem. Int. Ed. 2021; 60: 12904

For selected examples, see:
• 6a Yan LZ, Dawson PE. J. Am. Chem. Soc. 2001; 123: 526
• 6b Wan Q, Danishefsky SJ. Angew. Chem. Int. Ed. 2007; 46: 9248
• 6c Wang S, Thopate YA, Zhou Q, Wang P. Chin. J. Chem. 2019; 37: 1181
• 6d Giesler RJ, Erickson PW, Kay MS. Curr. Opin. Chem. Biol. 2020; 58: 37
• 6e Wang S, Zhou Q, Li Y, Wei B, Liu X, Zhao J, Ye F, Zhou Z, Ding B, Wang P. J. Am. Chem. Soc. 2022; 144: 1232
• 7 Shin NY, Ryss JM, Zhang X, Miller SJ, Knowles RR. Science 2019; 366: 364

For selected examples, see:
• 8a Tan Z, Shang S, Danishefsky SJ. Angew. Chem. Int. Ed. 2010; 49: 9500
• 8b Malins LR, Giltrap AM, Dowman LJ, Payne RJ. Org. Lett. 2015; 17: 2070
• 8c Kulkarni SS, Sayers J, Premdjee B, Payne RJ. Nat. Rev. Chem. 2018; 2: 0122
• 9a Seebach D, Sting AR, Hoffmann M. Angew. Chem. Int. Ed. 1996; 35: 2708
• 9b Polt R, Seebach D. J. Am. Chem. Soc. 1989; 111: 2622
• 9c Jeanguenat A, Seebach D. J. Chem. Soc., Perkin Trans. 1 1991; 2291
• 10 Yin H, Zheng M, Chen H, Wang S, Zhou Q, Zhang Q, Wang P. J. Am. Chem. Soc. 2020; 142: 14201
• 11 McCaldon P, Argos P. Proteins 1988; 4: 99
• 12a Bootsma AN, Doney AC, Wheeler SE. J. Am. Chem. Soc. 2019; 141: 11027
• 12b Heringa J, Argos P. J. Mol. Biol. 1991; 220: 151
• 13a Crich D, Banerjee A. J. Am. Chem. Soc. 2007; 129: 10064
• 13b Malins LR, Giltrap AM, Dowman LJ, Payne RJ. Org. Lett. 2015; 17: 2070
• 13c Morishita Y, Kaino T, Okamoto R, Izumi M, Kajihara Y. Tetrahedron Lett. 2015; 56: 6565
• 14a Andrieux CP, Blocman C, Dumas-Bouchiat JM, Saveant JM. J. Am. Chem. Soc. 1979; 101: 3431
• 14b Costentin C, Robert M, Savéant J.-M. J. Am. Chem. Soc. 2004; 126: 16051
• 14c Nguyen JD, D’Amato EM, Narayanam JM. R, Stephenson CR. J. Nat. Chem. 2012; 4: 854
• 14d Ghosh I, Ghosh T, Bardagi Javier I, König B. Science 2014; 346: 725
• 15 Rosso JA, Bertolotti SG, Braun AM, Mártire DO, Gonzalez MC. J. Phys. Org. Chem. 2001; 14: 300

For selected examples, see:
• 16a Wang H, Gao Y, Zhou C, Li G. J. Am. Chem. Soc. 2020; 142: 8122
• 16b Flynn AR, McDaniel KA, Hughes ME, Vogt DB, Jui NT. J. Am. Chem. Soc. 2020; 142: 9163
• 16c Huang H.-M, Bellotti P, Erchinger JE, Paulisch TO, Glorius F. J. Am. Chem. Soc. 2022; 144: 1899
• 16d Chmiel AF, Williams OP, Chernowsky CP, Yeung CS, Wickens ZK. J. Am. Chem. Soc. 2021; 143: 10882
• 17a Kingsbury CL, Sharp KS, Smith RA. J. Tetrahedron 1999; 55: 14693
• 17b House HO, Chu C.-Y, Wilkins JM, Umen MJ. J. Org. Chem. 1975; 40: 1460
• 17c Bertz SH, Gibson CP, Dabbagh G. Tetrahedron Lett. 1987; 28: 4251
• 17d Dambacher J, Bergdahl M. J. Org. Chem. 2005; 70: 580
• 18a Kleijn H, Elsevier CJ, Westmijze H, Meijer J, Vermeer P. Tetrahedron Lett. 1979; 20: 3101
• 18b Marfat A, McGuirk PR, Helquist P. J. Org. Chem. 1979; 44: 3888
• 19 Moschner J, Stulberg V, Fernandes R, Huhmann S, Leppkes J, Koksch B. Chem. Rev. 2019; 119: 10718
• 20 Wang S, Zhou Q, Chen X, Luo R.-H, Li Y, Liu X, Yang L.-M, Zheng Y.-T, Wang P. Nat. Commun. 2021; 12: 2257
• 21 Gracia-Vitoria J, Osante I, Cativiela C, Merino P, Tejero T. J. Org. Chem. 2018; 83: 3960