Modular Synthesis of New Pyrroloquinoline Quinone Derivatives

Abstract

Pyrroloquinoline quinone (PQQ) is an important cofactor of methanol dehydrogenases and glycose dehydrogenases. In addition, isolated PQQ is used as a central component in sensors and biomimetic complexes. The synthesis of PQQ derivatives is of interest for developing new alcohol oxidation catalysts and redox sensors. This work describes a modular synthesis for derivatives of PQQ bearing methyl and ketone groups instead of carboxylic acid moieties. These modifications reduce the possible coordination sites of PQQ for metal ions outside the protein environment.

Key words

redox cofactor - pyrroloquinoline quinone - alcohol oxidation - pincer ligand - natural product derivatives

Publication History

Received: 28 August 2022

Accepted after revision: 19 September 2022

Article published online:
07 November 2022

• References

• 1a Duine JA, van der Meer RA, Groen BW. Annu. Rev. Nutr. 1990; 10: 297
• 1b Duine JA. J. Biosci. Bioeng. 1999; 88: 231
• 1c Anthony C. Antioxid. Redox Signal. 2001; 3: 804
• 1d Akagawa M, Nakano M, Ikemoto K. Biosci. Biotechnol. Biochem. 2016; 80: 13
• 1e Sarmiento-Pavía PD, Sosa-Torres ME. J. Biol. Inorg. Chem. 2021; 26: 177
• 2a Guo Z, Smutok O, Johnston WA, Ayva CE, Walden P, McWhinney B, Ungerer JP. J, Melman A, Katz E, Alexandrov K. Angew. Chem. Int. Ed. 2022; 61: e202109005
• 2b Lee H, Hong YJ, Baik S, Hyeon T, Kim DH. Adv. Healthcare Mater. 2018; 7: 1
• 3a Anthony C, Ghosh M, Blake CC. F. Biochem. J. 1994; 304: 665
• 3b Pol A, Barends TR. M, Dietl A, Khadem AF, Eygensteyn J, Jetten MS. M, Op den Camp HJ. M. Environ. Microbiol. 2014; 16: 255
• 4a Satheeshkumar K, Kumar PS, Nandhini C, Shanmugapriya R, Vennila KN, Elango KP. Inorg. Chem. Commun. 2022; 139: 109299
• 4b Takeda K, Kusuoka R, Inukai M, Igarashi K, Ohno H, Nakamura N. Biosens. Bioelectron. 2021; 112831
• 4c Lumpe H, Menke A, Haisch C, Mayer P, Kabelitz A, Yusenko KV, Guilherme Buzanich A, Block T, Pöttgen R, Emmerling F, Daumann LJ. Chem. Eur. J. 2020; 26: 10133
• 5a Vetsova VA, Fisher KR, Lumpe H, Schäfer A, Schneider EK, Weis P, Daumann LJ. Chem. Eur. J. 2021; 27: 10087
• 5b Schäfer A, Vetsova VA, Schneider EK, Kappes M, Seitz M, Daumann LJ, Weis P. J. Am. Soc. Mass Spectrom. 2022; 33: 722
• 5c Lumpe H, Daumann LJ. Inorg. Chem. 2019; 58: 8432
• 6 Nevarez JL, Turmo A, Hu J, Hausinger RP. ChemCatChem 2020; 12: 4242
• 7a Lumpe H, Mayer P, Daumann LJ. Acta Crystallogr. Sect. C 2020; 76: 1051
• 7b Ikemoto K, Sakamoto Y, Tanaka R, Ogata K, Matsushita N, Nakamura S. Cryst. Growth Des. 2017; 17; 4118
• 7c Ishida T, Doi M, Tomita K, Hayashi H, Inoue M, Urakami T. J. Am. Chem. Soc. 1989; 111; 6822
• 8 Zhang Z, Tillekeratne LM. V, Hudson RA. Synthesis 1996; 377
• 9 Corey EJ, Tramontano A. J. Am. Chem. Soc. 1981; 103: 5599
• 10a Itoh S, Ogino M, Fukui Y, Murao H, Komatsu M, Ohshiro Y, Inoue T, Kai Y, Kasai N. J. Am. Chem. Soc. 1993; 115: 9960
• 10b Itoh S, Kawakami H, Fukuzumi S. J. Am. Chem. Soc. 1997; 119: 439
• 10c Itoh S, Kawakami H, Fukuzumi S. Biochemistry 1998; 37: 6562
• 11a Büchi G, Botkin JH, Lee GC. M, Yakushijin K. J. Am. Chem. Soc. 1985; 107: 5555
• 11b MacKenzie AR, Moody CJ, Rees CW. Tetrahedron 1986; 42: 3259
• 11c Gainor JA, Weinreb SM. J. Org. Chem. 1982; 47: 2833
• 11d Glinkerman CM, Boger DL. J. Am. Chem. Soc. 2016; 138: 12408
• 11e Hendrickson JB, de Vries JG. J. Org. Chem. 1985; 50: 1688
• 11f Lewis JA, DiNardo JC. US 2014/0178316 A1, 2014
• 11g Kempf JV, Gopal D, Stalzer W. US 2007/0072894 A1, 2007
• 12 Ameyama M, Hayashi M, Matsushita K, Shinagawa E, Adachi O. Agric. Biol. Chem. 1984; 48: 561
• 13 Trotta AH. Org. Lett. 2015; 17: 3358
• 14 Fischer E, Jourdan F. Ber. Dtsch. Chem. Ges. 1883; 16: 2241
• 15 Doebner O, v. Miller W. Ber. Dtsch. Chem. Ges. 1883; 16: 2464
• 16 CCDC 2193479 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures