Biomimetic in situ Regeneration of Cofactors NAD(P)+ and NAD(P)H Models Hantzsch Esters and Dihydrophenanthridine

Wangming Du; Zhengkun Yu

doi:10.1055/s-0031-1291005

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(9): 1300-1304
DOI: 10.1055/s-0031-1291005

new tools in synthesis

Biomimetic in situ Regeneration of Cofactors NAD(P)⁺ and NAD(P)H Models Hantzsch Esters and Dihydrophenanthridine

Wangming Du

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, Liaoning 116023, P. R. of China, Fax: +86(411)84379227 eMail: zkyu@dicp.ac.cn

,

Zhengkun Yu*

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, Liaoning 116023, P. R. of China, Fax: +86(411)84379227 eMail: zkyu@dicp.ac.cn

› Institutsangaben

Abstract

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Abstract

Biomimetic recycling of the expensive cofactors NAD(P)H/NAD(P)⁺and their models is a promising area in bio-inspired synthesis. This paper highlights the recent advances in the in situ regeneration of the oxidized cofactors NAD(P)⁺ through oxidation of cofactors NAD(P)H in the presence of an alcohol dehydrogenase by means of dioxygen and a synthetic Fe(III) porphyrin as a biomimetic NAD(P)H oxidase or flavin as catalyst, and biomimetic in situ regeneration of the expensive NAD(P)H models Hantzsch esters (HEH) and 9,10-dihydrophenanthridine (DHPD) by transition-metal and chiral Brønsted acid catalyzed relay asymmetric hydrogenation.

1. Introduction

2. Biomimetic in situ Regeneration of NAD(P)⁺

3. Biomimetic in situ Regeneration of Hantzsch Esters (HEH)

4. Biomimetic in situ Regeneration of Dihydrophenanthridine (DHPD)

5. Future Perspective

Key words

biomimetic - regeneration - asymmetric hydrogenation - Hantzsch esters - dihydrophenanthridine

Volltext

Referenzen

References
1 Frey PA, Hegeman AD. Enzymatic Reaction Mechanisms . Oxford University Press; New York: 2007
2 Hantzsch A. Ber. Dtsch. Chem. Ges. 1881; 14: 1637
3 Hanztsch A. Justus Liebigs Ann. Chem. 1882; 215: 1
4 Woodyer R, Zhao HM, van der Donk WA. FEBS J. 2005; 272: 3816
5 De Vries JG, Mršić N. Catal. Sci. Technol. 2011; 1: 727
6 Chen Q.-A, Wang D.-S, Zhou Y.-G, Duan Y, Fan H.-J, Yang Y, Zhang Z. J. Am. Chem. Soc. 2011; 133: 6126
7 Pelletier G, Bechara WS, Charette A. J. Am. Chem. Soc. 2010; 132: 12817
8 Martin NJ. A, Ozores L, List B. J. Am. Chem. Soc. 2007; 129: 8976
9 Li G, Liang Y, Antilla JC. J. Am. Chem. Soc. 2007; 129: 5830
10 Hoffmann S, Nicoletti M, List B. J. Am. Chem. Soc. 2006; 128: 13074
11 Tuttle JB, Ouellet SG, MacMillan DW. C. J. Am. Chem. Soc. 2006; 128: 12662
12 Ouellet SG, Tuttle JB, MacMillan DW. C. J. Am. Chem. Soc. 2005; 127: 32
13 Hall M, Bommarius AS. Chem. Rev. 2011; 111: 4088
14 Rueping M, Sugiono E, Schoepke FR. Synlett 2010; 852
15 You S.-L. Chem.–Asian. J. 2007; 2: 820
16 Ouellet SG, Walji AM, MacMillan DW. C. Acc. Chem. Res. 2007; 40: 1327
17 Weckbecker A, Gröger H, Hummel W. Adv. Biochem. Eng./Biotechnol. 2010; 120: 195
18 Schroer K, Luef KP, Hartner FS, Glieder A, Pscheidt B. Metabol. Eng. 2010; 12: 8
19 Zhao HM. ACS Catal. 2011; 1: 1119
20 Wischang D, Brücher O, Hartung J. Coord. Chem. Rev. 2011; 255: 2204
21 Pan YH, Tan CH. Synthesis 2011; 2044
22 Schröder K, Join B, Amali AJ, Junge K, Ribas X, Costas M, Beller M. Angew. Chem. Int. Ed. 2011; 50: 1425
23 Xiao X, Xie Y, Su CX, Liu M, Shi YA. J. Am. Chem. Soc. 2011; 133: 12914
24 Sugano Y, Vestergaard MC, Saito M, Tamiya E. Chem. Commun. 2011; 7176
25 Bhoware SS, Kim KY, Kim JA, Wu Q, Kim J. J. Phys. Chem. C 2011; 115: 2553
26 Gargiulo S, Arends IW. C. E, Hollmann F. ChemCatChem 2011; 3: 338
27 Haquette P, Talbi B, Barilleau L, Madern N, Fosse C, Salmain M. Org. Biomol. Chem. 2011; 9: 5720
28 Sambongi Y, Nitta H, Ichihashi K, Futai M, Ueda I. J. Org. Chem. 2002; 67: 3499
29 Hummel W, Kuzu M, Geueke B. Org. Lett. 2003; 5: 3649
30 Pival SL, Klimacek M, Nidetzky B. Adv. Synth. Catal. 2008; 350: 2305
31 Lee HJ, Lee SH, Park CB, Won K. Chem. Commun. 2011; 47: 12538
32 Hilt G, Lewall B, Montero G, Utley JH. P, Steckhan E. Liebigs Ann./Recl. 1997; 2289
33 Wakchaure VN, Zhou J, Hoffmann S, List B. Angew. Chem. Int. Ed. 2010; 49: 4612
34 Maid H, Böhn P, Huber SM, Bauer W, Hummel W, Jux N, Gröger H. Angew. Chem. Int. Ed. 2011; 50: 2397
35 Chen Q.-A, Chen M.-W, Yu C.-B, Shi L, Wang D.-S, Yang Y, Zhou Y.-G. J. Am. Chem. Soc. 2011; 133: 16432
36 Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557
37 Kuwano R. Heterocycles 2008; 76: 909
38 Zhou Y.-G. Acc. Chem. Res. 2007; 40: 1357
39 Tang WJ, Zhang XM. Chem. Rev. 2003; 103: 3029
40 Rueping M, Antonchick AP, Theissmann T. Angew. Chem. Int. Ed. 2006; 45: 6751
41 Chen Q.-A, Gao K, Duan Y, Ye Z.-S, Shi L, Yang Y, Zhou Y.-G. J. Am. Chem. Soc. 2012; 134: 2442