Chemoenzymatic synthesis of carbohydrates as antidiabetic and anticancer drugs

Current Topics in Medicinal Chemistry

Volumn 14, Issue 23, 2014, Pages 2694-2711

  Alcántara, Andrés R ^a   Pace, Vittorio ^b   Hoyos, Pilar ^a   Sandoval, Manuel ^c   Holzer, Wolfgang ^b   Hernáiz, María J ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF VIENNA   (Austria)

^c UNIVERSIDAD NACIONAL   (Costa Rica)

Author keywords

Anticancer drugs; Antidiabetic drugs; Biocatalysis; Carbohydrates; Glycomimetic

Indexed keywords

1 DEOXYMANNONOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN; 2 5 DIDEOXY 2 5 IMINO D MANNITOL; ACARBOSE; ALEXINE; ALPHA GLUCOSIDASE INHIBITOR; AMINOCYCLITOL; ANTIDIABETIC AGENT; ANTINEOPLASTIC AGENT; AUSTRALINE; CALYSTEGINE A3; CASTANOSPERMINE; CASUARINE; CHROMOMYCIN A3; FAGOMINE; FRUCTOSE BISPHOSPHATE ALDOLASE; GLYCOSIDASE; HYACINTHACINE; IMINOCYCLITOL; INDOLIZIDINE ALKALOID; MIGLITOL; MIGLUSTAT; MITHRAMYCIN; NOJIRIMYCIN; ORGANIC COMPOUND; PYRROLIZINE DERIVATIVE; SWAINSONINE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VOGLIBOSE; BACTERIAL PROTEIN; BIOMIMETIC MATERIAL; FUNGAL PROTEIN; GLYCOCONJUGATE; LYASE;

ACYLATION; ANTIDIABETIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BIOTRANSFORMATION; CARBOHYDRATE SYNTHESIS; CHEMOENZYMATIC SYNTHESIS; CLINICAL TRIAL (TOPIC); HUMAN; RACEMIZATION; TRANSESTERIFICATION; CANDIDA; CHEMISTRY; ENZYMOLOGY; GENETICS; GLUCONOBACTER OXYDANS; METABOLISM; PROTEIN ENGINEERING; PSEUDOMONAS; SYNTHESIS;

ALDEHYDE-LYASES; ANTINEOPLASTIC AGENTS; BACTERIAL PROTEINS; BIOMIMETIC MATERIALS; BIOTRANSFORMATION; CANDIDA; FUNGAL PROTEINS; GLUCONOBACTER OXYDANS; GLYCOCONJUGATES; GLYCOSIDE HYDROLASES; HUMANS; HYPOGLYCEMIC AGENTS; LIPASE; PROTEIN ENGINEERING; PSEUDOMONAS;

EID: 84926321639     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026614666141215151056     Document Type: Article

References (117)

1. [1] Ernst, B.; Magnani, J.L. From carbohydrate leads to glycomimetic drugs. Nat. Rev. Drug Discov., 2009, 8, (8), 661-677.
2. [2] Nestl, B.M.; Hammer, S.C.; Nebel, B.A.; Hauer, B. New Generation of Biocatalysts for Organic Synthesis. Angew. Chem., Int. Edit., 2014, 53, (12), 3070-3095.
3. [3] Hernáiz, M.J.; Crout, D.H.G. A highly selective synthesis of Nacetyllactosamine catalyzed by immobilised beta-galactosidase from Bacillus circulans. J. Mol. Catal. B-Enzym., 2000, 10, (4), 403-408.
4. [4] Bayón, C.; Cortés, A.; Aires-Trapote, A.; Civera, C.; Hernáiz, M.J. Highly efficient and regioselective enzymatic synthesis of beta-(1-> 3) galactosides in biosolvents. RSC Adv., 2013, 3, (30), 12155-12163.
5. [5] Pérez-Sánchez, M.; Sandoval, M.; Cortés-Cabrera, A.; García-Marín, H.; Sinisterra, J.V.; García, J.I.; Hernáiz, M.J. Solvents derived from glycerol modify classical regioselectivity in the enzymatic synthesis of disaccharides with Biolacta beta-galactosidase. Green Chem., 2011, 13, (10), 2810-2817.
6. [6] Hoyos, P.; Pace, V.; Hernáiz, M.J.; Alcántara, A.R. Biocatalysis in the Pharmaceutical Industry. A greener future. Curr. Green Chem., 2014, 1, (2), 155-181.
7. [7] World Health Statistics; Global Health Observatory (GHO), World Health Organization: 2012.
8. [8] Jemal, A.; Bray, F.; Center, M.M.; Ferlay, J.; Ward, E.; Forman, D. Global Cancer Statistics. CA-Cancer J. Clin., 2011, 61, (2), 69-90.
9. [9] Campo, V.L.; Aragao-Leoneti, V.; Carvalho, I. In Carbohydrate Chemistry: Chemical and Biological Approaches, Vol 39. Rauter, A.P.; Lindhorst, T.K., Eds.; Royal Soc Chemistry: Cambridge, 2013; Vol. 39, pp 181-203.
10. [10] Horne, G.; Wilson, F.X.; Tinsley, J.; Williams, D.H.; Storer, R. Iminosugars past, present and future: medicines for tomorrow. Drug Discov. Today, 2011, 16, (3–4), 107-118.
11. [11] Winchester, B.G. Iminosugars: from botanical curiosities to licensed drugs. Tetrahedron-Asymmetry, 2009, 20, (6-8), 645-651.
12. [12] Witczak, Z.J.; Culhane, J.M. Thiosugars: new perspectives regarding availability and potential biochemical and medicinal applications. Appl. Microbiol. Biotechnol., 2005, 69, (3), 237-244.
13. [13] Mayato, C.; Dorta, R.L.; Palazón, J.M.; Vázquez, J.T. Comparison of the conformational properties of carbasugars and glycosides: the role of the endocyclic oxygen. Carbohydr. Res., 2012, 352, 101-108.
14. [14] Caines, M.E.C.; Hancock, S.M.; Tarling, C.A.; Wrodnigg, T.M.; Stick, R.V.; Stutz, A.E.; Vasella, A.; Withers, S.G.; Strynadka, N.C.J. The structural basis of glycosidase inhibition by fivemembered iminocyclitols: The clan A glycoside hydrolase endoglycoceramidase as a model system. Angew. Chem., Int. Edit., 2007, 46, (24), 4474-4476.
15. [15] Horne, G.; Wilson, F.X. In Progress in Medicinal Chemistry, Vol 50. Lawton, G.; Witty, D.R., Eds.; Elsevier Science Bv: Amsterdam, 2011; Vol. 50, pp 135-176.
16. [16] Mitrakou, A.; Tountas, N.; Raptis, A.E.; Bauer, R.J.; Schulz, H.; Raptis, S.A. Long-term effectiveness of a new alpha-glucosidase inhibitor (BAY m1099-Miglitol) in insulin-treated Type 2 diabetes mellitus. Diabetic Med., 1998, 15, (8), 657-660.
17. [17] Derosa, G.; Maffioli, P. Alpha-Glucosidase inhibitors and their use in clinical practice. Arch. Med. Sci., 2012, 8, (5), 899-906.
18. [18] Lahiri, R.; Ansari, A.A.; Vankar, Y.D. Recent developments in design and synthesis of bicyclic azasugars, carbasugars and related molecules as glycosidase inhibitors. Chem. Soc. Rev., 2013, 42, (12), 5102-5118.
19. [19] Asano, N.; Nash, R.J.; Molyneux, R.J.; Fleet, G.W.J. Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application. Tetrahedron-Asymmetry, 2000, 11, (8), 1645-1680.
20. [20] Wardrop, D.J.; Waidyarachchi, S.L. Synthesis and biological activity of naturally occurring alpha-glucosidase inhibitors. Nat. Prod. Rep., 2010, 27, (10), 1431-1468.
21. [21] Kinast, G.; Schedel, M. Preparation of 1-desoxy-nojirimycin and derivatives by microbial oxidation of 1-amino-1-desoxy-D-glucitol derivatives and catalytic hydrogenation. European Patent 12,278-A, June 25, 1980.
22. [22] Kinast, G.; Schedel, M. 6-Amino-6-desoxy-L-sorbose production by microbial conversion of 6-desoxy-D-glucitol. European Patent 8,031A, February 14, 1980.
23. [23] Kinast, G.; Schedel, M. A 4-step synthesis of 1-deoxynojirimycin with a biotransformation as cardinal reaction step. Angew. Chem., Int. Edit., 1981, 20, (9), 805-806.
24. [24] Kinast, G.; Schedel, M.; Koebernick, W. Preparation of 1-desoxynojirimycin compounds from 1-amino-sorbitol compunds via 6-amino-sorbose compounds. European Patent 49,858-A, April 21, 1982.
25. [25] Zhang, J.B.; Zhang, X.L.; Wang, D.H.; Zhao, B.X.; He, G. In New and Advanced Materials, Pts 1 and 2. Zhou, H.Y.; Gu, T.L.; Yang, D.G.; Jiang, Z.Y.; Zeng, J.M., Eds.; Trans Tech Publications Ltd: Stafa-Zurich, 2011; Vol. 197-198, pp 51-55.
26. [26] Clark, L.F.; Johnson, J.V.; Horenstein, N.A. Identification of a Gene Cluster that Initiates Azasugar Biosynthesis in Bacillus amyloliquefaciens. ChemBiochem., 2011, 12, (14), 2147-2150.
27. [27] Chen, X.H.; Koumoutsi, A.; Scholz, R.; Eisenreich, A.; Schneider, K.; Heinemeyer, I.; Morgenstern, B.; Voss, B.; Hess, W.R.; Reva, O.; Junge, H.; Voigt, B.; Jungblut, P.R.; Vater, J.; Sussmuth, R.; Liesegang, H.; Strittmatter, A.; Gottschalk, G.; Borriss, R., Comparative analysis of the complete genome sequence of the plant growth-promoting bacterium Bacillus amyloliquefaciens FZB42. Nat. Biotechnol., 2007, 25, (9), 1007-1014.
28. [28] Wu, Y.B.; Arciola, J.; Horenstein, N., Medium-Chain Dehydrogenases with New Specificity: Amino Mannitol Dehydrogenases on the Azasugar Biosynthetic Pathway. Protein Pept. Lett., 2014, 21, (1), 10-14.
29. [29] Yu, Z.Q.; Sawkar, A.R.; Whalen, L.J.; Wong, C.H.; Kelly, J.W. Isofagomine-and 2,5-anhydro-2,5-imino-D-glucitol-based glucocerebrosidase pharmacological chaperones for Gaucher disease intervention. J. Med. Chem., 2007, 50, (1), 94-100.
30. [30] Durrwachter, J.R.; Wong, C.H. Fructose 1,6-diphosphate aldolase catalyzed stereoselective synthesis of C-alkyl and N-containing sugars. Thermodynamically controlled C-C bond formations. J. Org. Chem., 1988, 53, (18), 4175-4181.
31. [31] Ziegler, T.; Straub, A.; Effenberger, F. Enzyme-catalyzed reactions.3. Enzyme-catalyzed synthesis of 1-deoxymannojirimycin, 1-deoxynojirimycin, and 1,4-dideoxy-1,4-imino-D-arabinitol. Angew. Chem., Int. Edit., 1988, 27, (5), 716-717.
32. [32] Pederson, R.L.; Kim, M.J.; Wong, C.H. A combined chemical and enzymatic procedure for the synthesis of 1-deoxynojirimycin and 1-deoxymannojirimycin. Tetrahedron Lett., 1988, 29, (37), 4645-4648.
33. [33] Von der Osten, C.H.; Sinskey, A.J.; Barbas, C.F.; Pederson, R.L.; Wang, Y.F.; Wong, C.H. Use of a recombinant bacterial fructose-1,6-diphosphate aldolase in aldol reactions. Preparative syntheses of 1-deoxynojirimycin, 1-deoxymannojirimycin, 1,4-dideoxy-1,4-imino-D-arabinitol, and fagomine. J. Am. Chem. Soc., 1989, 111, (11), 3924-3927.
34. [34] Straub, A.; Effenberger, F.; Fischer, P. Enzyme-catalyzed reactions.4. Aldolase-catalyzed C-C bond formation for stereoselective synthesis of nitrogen-containing carbohydrates. J. Org. Chem., 1990, 55, (12), 3926-3932.
35. [35] Kajimoto, T.; Chen, L.R.; Liu, K.K.C.; Wong, C.H. Palladiummediated stereocontrolled reductive amination of azido sugars prepared from enzymatic aldol condensation. A general approach to the synthesis of deoxy aza sugars. J. Am. Chem. Soc., 1991, 113, (17), 6678-6680.
36. [36] Kajimoto, T.; Liu, K.K.C.; Pederson, R.L.; Zhong, Z.Y.; Ichikawa, Y.; Porco, J.A.; Wong, C.H. Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars. Synthesis, evaluation, and modeling of glycosidase inhibitors. J. Am. Chem. Soc., 1991, 113, (16), 6187-6196.
37. [37] Liu, K.K.C.; Kajimoto, T.; Chen, L.R.; Zhong, Z.Y.; Ichikawa, Y.; Wong, C.H. Use of dihydroxyacetone phosphate dependent aldolases in the synthesis of deoxyazasugars. J. Org. Chem., 1991, 56, (22), 6280-6289.
38. [38] Fiskesund, R.; Abeyama, K.; Yoshinaga, K.; Abe, J.; Yuan, Y.B.; Yu, S.K. 1,5-Anhydro-D-Fructose and its Derivatives: Biosynthesis, Preparation and Potential Medical Applications. Planta. Med., 2010, 76, (15), 1635-1641.
39. [39] Calveras, J.; Egido-Gabas, M.; Gomez, L.; Casas, J.; Parella, T.; Joglar, J.; Bujons, J.; Clapes, P. Dihydroxyacetone Phosphate Aldolase Catalyzed Synthesis of Structurally Diverse Polyhydroxylated Pyrrolidine Derivatives and Evaluation of their Glycosidase Inhibitory Properties. Chem. Eur. J., 2009, 15, (30), 7310-7328.
40. [40] Espelt, L.; Parella, T.; Bujons, J.; Solans, C.; Joglar, J.; Delgado, A.; Clapes, P. Stereoselective aldol additions catalyzed by dihydroxyacetone phosphate-dependent aldolases in emulsion systems: Preparation and structural characterization of linear and cyclic iminopolyols from aminoaldehydes. Chem. Eur. J., 2003, 9, (20), 4887-4899.
41. [41] Espelt, L.; Clapes, P.; Esquena, J.; Manich, A.; Solans, C. Enzymatic carbon-carbon bond formation in water-in-oil highly concentrated emulsions (gel emulsions). Langmuir, 2003, 19, (4), 1337-1346.
42. [42] Espelt, L.; Bujons, J.; Parella, T.; Calveras, J.; Joglar, J.; Delgado, A.; Clapes, P. Aldol additions of dihydroxyacetone phosphate to NCbz-amino aldehydes catalyzed by L-fuculose-1-phosphate aldolase in emulsion systems: Inversion of stereoselectivity as a function of the acceptor aldehyde. Chem. Eur. J., 2005, 11, (5), 1392-1401.
43. [43] Babich, L.; van Hemert, L.J.C.; Bury, A.; Hartog, A.F.; Falcicchio, P.; van der Oost, J.; van Herk, T.; Wever, R.; Rutjes, F.P.J.T. Synthesis of non-natural carbohydrates from glycerol and aldehydes in a one-pot four-enzyme cascade reaction. Green Chem., 2011, 13, (10), 2895-2900.
44. [44] Babich, L.; Hartog, A.F.; van Hemert, L.J.C.; Rutjes, F.P.J.T.; Wever, R. Synthesis of Carbohydrates in a Continuous Flow Reactor by Immobilized Phosphatase and Aldolase. Chem Sus Chem., 2012, 5, (12), 2348-2353.
45. [45] Samland, A.K.; Rale, M.; Sprenger, G.A.; Fessner, W.D. The Transaldolase Family: New Synthetic Opportunities from an Ancient Enzyme Scaffold. Chem Biochem., 2011, 12, (10), 1454-1474.
46. [46] Castillo, J.A.; Calveras, J.; Casas, J.; Mitjans, M.; Vinardell, M.P.; Parella, T.; Inoue, T.; Sprenger, G.A.; Joglar, J.; Clapes, P. Fructose-6-phosphate aldolase in organic synthesis: Preparation of Dfagomine, N-alkylated derivatives, and preliminary biological assays. Org. Lett., 2006, 8, (26), 6067-6070.
47. [47] Clapes, P.; Joglar, J.; Castillo, J.A.; Lozano, C. Preparing iminocyclitol compound, e.g. as dietary supplements, comprises aldol addition catalyzed by D-fructose-6-phosphate aldolase enzyme and acceptor aminoaldehyde compound, followed by intramolecular reductive amination with hydrogen. WO Patent 2008025826-A1, March 06, 2008.
48. [48] Gomez, L.; Molinar-Toribio, E.; Calvo-Torras, M.A.; Adelantado, C.; Juan, M.E.; Planas, J.M.; Canas, X.; Lozano, C.; Pumarola, S.; Clapes, P.; Torres, J.L. D-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion. Br. J. Nutr., 2012, 107, (12), 1739-1746.
49. [49] Concia, A.L.; Lozano, C.; Castillo, J.A.; Parella, T.; Joglar, J.; Clapes, P. D-Fructose-6-phosphate Aldolase in Organic Synthesis: Cascade Chemical-Enzymatic Preparation of Sugar-Related Polyhydroxylated Compounds. Chem. Eur. J., 2009, 15, (15), 3808-3816.
50. [50] Sugiyama, M.; Hong, Z.; Liang, P.-H.; Dean, S.M.; Whalen, L.J.; Greenberg, W.A.; Wong, C.-H. D-Fructose-6-phosphate aldolasecatalyzed one-pot synthesis of iminocyclitols. J. Am. Chem. Soc., 2007, 129, (47), 14811-14817.
51. [51] Saludes, J.P.; Lievens, S.C.; Molinski, T.F. Occurrence of the alpha-glucosidase inhibitor 1,4-dideoxy-1,4-imino-D-arabinitol and related iminopentitols in marine sponges. J. Nat. Prod., 2007, 70, (3), 436-438.
52. [52] Walls, A.B.; Sickmann, H.M.; Brown, A.; Bouman, S.D.; Ransom, B.; Schousboe, A.; Waagepetersen, H.S. Characterization of 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) as an inhibitor of brain glycogen shunt activity. J. Neurochem., 2008, 105, (4), 1462-1470.
53. [53] Andersen, B.; Rassov, A.; Westergaard, N.; Lundgren, K. Inhibition of glycogenolysis in primary rat hepatocytes by 1,4-dideoxy-1,4-imino-D-arabinitol. Biochem. J., 1999, 342, 545-550.
54. [54] Praly, J.P.; Vidal, S. Inhibition of Glycogen Phosphorylase in the Context of Type 2 Diabetes, with Focus on Recent Inhibitors Bound at the Active Site. Mini-Rev. Med. Chem., 2010, 10, (12), 1102-1126.
55. [55] Provencher, L.; Steensma, D.H.; Wong, C.H. Five-membered ring azasugars as potent inhibitors of alpha-L-rhamnosidase (naringinase) from Penicillium decumbens. Bioorg. Med. Chem., 1994, 2, (11), 1179-1188.
56. [56] Wang, Y.F.; Dumas, D.P.; Wong, C.H. Chemoenzymatic synthesis of 5-membered azasugars as inhibitors of fucosidase and fucosyltransferase-an issue regarding the stereochemistry discrimination at transition-states. Tetrahedron Lett., 1993, 34, (3), 403-406.
57. [57] Takaoka, Y.; Kajimoto, T.; Wong, C.H. Inhibition of Nacetylglucosaminyltransfer enzymes. Chemical-enzymatic synthesis of new 5-membered acetamido azasugars. J. Org. Chem., 1993, 58, (18), 4809-4812.
58. [58] Wang, Y.F.; Takaoka, Y.; Wong, C.H. Remarkable stereoselectivity in the inhibition of alpha-galactosidase from coffee bean by a new polyhydroxypyrrolidine inhibitor. Angew. Chem., Int. Edit., 1994, 33, (12), 1242-1244.
59. [59] Takayama, S.; McGarvey, G.J.; Wong, C.H. Microbial aldolases and transketolases: new biocatalytic approaches to simple and complex sugars. Annu. Rev. Microbiol., 1997, 51, 285-310.
60. [60] Takayama, S.; Martin, R.; Wu, J.Y.; Laslo, K.; Siuzdak, G.; Wong, C.H. Chemoenzymatic preparation of novel cyclic imine sugars and rapid biological activity evaluation using electrospray mass spectrometry and kinetic analysis. J. Am. Chem. Soc., 1997, 119, (35), 8146-8151.
61. [61] Whalen, L.J.; Wong, C.H. Enzymes in organic synthesis: Aldolasemediated synthesis of iminocyclitols and novel heterocycles. Aldrichim. Acta, 2006, 39, (3), 63-71.
62. [62] Izquierdo, I.; Plaza, M.T.; Tamayo, J.A.; Franco, F.; Sanchez-Cantalejo, F., Polyhydroxylated pyrrolidines. Part VII-Lipasemediated synthesis of enantiomeric 2,5,6-trideoxy-2,5-iminohexitols. Tetrahedron, 2008, 64, (22), 4993-4998.
63. Izquierdo, I.; Plaza, M.T.; Tamayo, J.A.; Lo Re, D.; Sanchez-Cantalejo, F. Polyhydroxylated pyrrolidines: Synthesis of trideoxy-2,5-iminohexitols-Part VI. Synthesis, 2008, (9), 1373-1378.
64. [64] Usuki, H.; Toyo-oka, M.; Kanzaki, H.; Okuda, T.; Nitoda, T. Pochonicine, a polyhydroxylated pyrrolizidine alkaloid from fungus Pochonia suchlasporia var. suchlasporia TAMA 87 as a potent beta-N-acetylglucosaminidase inhibitor. Bioorg. Med. Chem., 2009, 17, (20), 7248-7253.
65. [65] Romero, A.; Wong, C.H. Chemo-enzymatic total synthesis of 3-epiaustraline, australine, and 7-epialexine. J. Org. Chem., 2000, 65, (24), 8264-8268.
66. [66] Calveras, J.; Casas, J.; Parella, T.; Joglar, J.; Clapes, P. Chemoenzymatic synthesis and inhibitory activities of hyacinthacines A(1) and A(2) stereoisomers. Adv. Synth. Catal., 2007, 349, (10), 1661-1666.
67. [67] Garrabou, X.; Gomez, L.; Joglar, J.; Gil, S.; Parella, T.; Bujons, J.; Clapes, P. Structure-Guided Minimalist Redesign of the LFuculose-1-Phosphate Aldolase Active Site: Expedient Synthesis of Novel Polyhydroxylated Pyrrolizidines and their Inhibitory Properties Against Glycosidases and Intestinal Disaccharidases. Chem. Eur. J., 2010, 16, (35), 10691-10706.
68. [68] Gomez, L.; Garrabou, X.; Joglar, J.; Bujons, J.; Parella, T.; Vilaplana, C.; Joan Cardona, P.; Clapes, P., Chemoenzymatic synthesis, structural study and biological activity of novel indolizidine and quinolizidine iminocyclitols. Org. Biomol. Chem., 2012, 10, (31), 6309-6321.
69. [69] Laborda, P.; Sayago, F.J.; Cativiela, C.; Parella, T.; Joglar, J.; Clapes, P., Aldolase-Catalyzed Synthesis of Conformationally Constrained Iminocyclitols: Preparation of Polyhydroxylated Benzopyrrolizidines and Cyclohexapyrrolizidines. Org. Lett., 2014, 16, (5), 1422-1425.
70. [70] Lesma, G.; Colombo, A.; Landoni, N.; Sacchetti, A.; Silvani, A., A chemoenzymatic-RCM strategy for the enantioselective synthesis of new dihydroxylated 5-hydroxymethyl-indolizidines and 6-hydroxymethyl-quinolizidines. Tetrahedron-Asymmetry, 2007, 18, (16), 1948-1954.
71. [71] Muramatsu, T.; Yamashita, S.; Nakamura, Y.; Suzuki, M.; Mase, N.; Yoda, H.; Takabe, K. Total synthesis of (-)-2-epi-lentiginosine by use of chiral 5-hydroxy-1,5-dihydropyrrol-2-one as a building block. Tetrahedron Lett., 2007, 48, (51), 8956-8959.
72. [72] Donohoe, T.J.; Rigby, C.L.; Thomas, R.E.; Nieuwenhuys, W.F.; Bhatti, F.L.; Cowley, A.R.; Bhalay, G.; Linney, I.D. An enzymatic approach to the desymmetrization of disubstituted pyrrolines. J. Org. Chem., 2006, 71, (16), 6298-6301.
73. [73] Tamayo, J.A.; Franco, F.; Lo Re, D.; Sanchez-Cantalejo, F. Synthesis of Pentahydroxylated Pyrrolizidines and Indolizidines. J. Org. Chem., 2009, 74, (15), 5679-5682.
74. [74] Wennekes, T.; Meijer, A.J.; Groen, A.K.; Boot, R.G.; Groener, J.E.; van Eijk, M.; Ottenhoff, R.; Bijl, N.; Ghauharali, K.; Song, H.; O'Shea, T.J.; Liu, H.L.; Yew, N.; Copeland, D.; van den Berg, R.J.; van der Marel, G.A.; Overkleeft, H.S.; Aerts, J.M. Dual-action lipophilic iminosugar improves glycemic control in obese rodents by reduction of visceral glycosphingolipids and buffering of carbohydrate assimilation. J. Med. Chem., 2010, 53, (2), 689-698.
75. [75] Kawamori, R.; Tajima, N.; Iwamoto, Y.; Kashiwagi, A.; Shimamoto, K.; Kaku, K. Voglibose for prevention of type 2 diabetes mellitus: a randomised, double-blind trial in Japanese individuals with impaired glucose tolerance. The Lancet, 2009, 373, (9675), 1607-1614.
76. [76] Chen, X.L.; Zheng, Y.G.; Shen, Y.C. Voglibose (Basen (R) AO-128), one of the most important alpha-glucosidase inhibitors. Curr. Med. Chem., 2006, 13, (1), 109-116.
77. [77] Kameda, Y.; Asano, N.; Yoshikawa, M.; Takeuchi, M.; Yamaguchi, T.; Matsui, K.; Horii, S.; Fukase, H. Valiolamine, a new alphaglucosidase inhibiting aminocyclitol produced by Streptomyces hygroscopicus. J. Antibiot., 1984, 37, (11), 1301-1307.
78. [78] Horii, S.; Fukase, H.; Kameda, Y. Stereoselective conversion of valienamine and validamine into valiolamine. Carbohydr. Res., 1985, 140, (2), 185-200.
79. [79] Quan, N.; Nie, L.D.; Zhu, R.H.; Shi, X.X.; Ding, W.; Lu, X., Total Syntheses of (+)-Valiolamine and (-)-1-epi-Valiolamine from Naturally Abundant (-)-Shikimic Acid. Eur. J. Org. Chem., 2013, 2013, (28), 6389-6396.
80. [80] Ji, L.; Zhang, D.F.; Zhao, Q.; Hu, S.M.; Qian, C.; Chen, X.Z. Diastereospecific epoxidation and highly regioselective ring-opening of (+)-valienamine: practical synthesis of (+)-valiolamine. Tetrahedron, 2013, 69, (34), 7031-7037.
81. [81] Shing, T.K.M.; Cheng, H.M. Intramolecular direct aldol reactions of sugar diketones: Syntheses of valiolamine and validoxylamine G. Org. Lett., 2008, 10, (18), 4137-4139.
82. [82] Zheng, Y.G.; Xue, Y.P.; Shen, Y.C. Production of valienamine by a newly isolated strain: Stenotrophomonas maltrophilia. Enzyme Microb. Technol., 2006, 39, (5), 1060-1065.
83. [83] Xue, Y.P.; Zheng, Y.G.; Shen, Y.C. Enhanced production of valienamine by Stenotrophomonas maltrophilia with fed-batch culture in a stirred tank bioreactor. Process Biochem., 2007, 42, (6), 1033-1038.
84. [84] El Blidi, L.; Crestia, D.; Gallienne, E.; Demuynck, C.; Bolte, J.; Lemaire, M. A straightforward synthesis of an aminocyclitol based on an enzymatic aldol reaction and a highly stereoselective intramolecular Henry reaction. Tetrahedron-Asymmetry, 2004, 15, (18), 2951-2954.
85. [85] El Blidi, L.; Ahbala, M.; Bolte, J.; Lemaire, M. Straightforward chemo-enzymatic synthesis of new aminocyclitols, analogues of valiolamine and their evaluation as glycosidase inhibitors. Tetrahedron-Asymmetry, 2006, 17, (18), 2684-2688.
86. [86] El Blidi, L.; Assaf, Z.; Bres, F.C.; Veschambre, H.; Thery, V.; Bolte, J.; Lemaire, M. Fructose-1,6-Bisphosphate Aldolase-Mediated Synthesis of Aminocyclitols (Analogues of Valiolamine) and their Evaluation as Glycosidase Inhibitors. ChemCatChem., 2009, 1, (4), 463-471.
87. [87] Bres, F.C.; Guerard-Helaine, C.; Fernandes, C.; Castillo, J.A.; Lemaire, M. Fructose-6-phosphate aldolases as versatile biocatalysts for nitrocyclitol syntheses. Tetrahedron-Asymmetry, 2013, 24, (18), 1075-1081.
88. [88] Zhou, X.H.; Qiao, Q.; Zethelius, B.; Pyörälä, K.; Söderberg, S.; Pajak, A.; Stehouwer, C.D.A.; Heine, R.J.; Jousilahti, P.; Ruotolo, G.; Nilsson, P.M.; Calori, G.; Tuomilehto, J. Diabetes, prediabetes and cancer mortality. Diabetol., 2010, 53, (9), 1867-1876.
89. [89] Li, C.; Kong, D. Cancer risks from diabetes therapies: Evaluating the evidence. Pharmacol. Ther., 2014, 144, (1), 71-81.
90. [90] Landman, G.W.D.; Van Hateren, K.J.J.; Kleefstra, N.; Bilo, H.J.G. The relationship between obesity and cancer mortality in type 2 diabetes: A ten-year follow-up study (ZODIAC-21). Anticancer Res., 2010, 30, (2), 681-682.
91. [91] Garg, S.K.; Maurer, H.; Reed, K.; Selagamsetty, R. Diabetes and cancer: Two diseases with obesity as a common risk factor. Diabetes Obes. Metab., 2014, 16, (2), 97-110.
92. [92] Hoyos, P.; Pace, V.; Alcántara, A.R. Biocatalyzed On Water Synthesis of Chiral Building Blocks for the Preparation of Anti-Cancer Drugs: a GreenerApproach. Curr. Org. Chem., 2013, 17, (11), 1132-1157.
93. [93] Calabresi, P.; Chabner, B.A. In The Pharmacological Basis of Therapeutics. Gilman, G., Ed.; MacMillan Publishing Co.: New York, 1991.
94. [94] Lombo, F.; Menendez, N.; Salas, J.A.; Mendez, C. The aureolic acid family of antitumor compounds: structure, mode of action, biosynthesis, and novel derivatives. Appl. Microbiol. Biotechnol., 2006, 73, (1), 1-14.
95. [95] Wohlert, S.E.; Künzel, E.; Machinek, R.; Méndez, C.; Salas, J.A.; Rohr, J. The Structure of Mithramycin Reinvestigated. J. Nat. Prod., 1998, 62, (1), 119-121.
96. [96] Snyder, R.C.; Ray, R.; Blume, S.; Miller, D.M. Mithramycin blocks transcriptional initiation of the c-myc P1 and P2 promoters. Biochemistry, 1991, 30, (17), 4290-4297.
97. [97] Chatterjee, S.; Zaman, K.; Ryu, H.; Conforto, A.; Ratan, R.R. Sequence-selective DNA binding drugs mithramycin A and chromomycin A3 are potent inhibitors of neuronal apoptosis induced by oxidative stress and DNA damage in cortical neurons. Ann. Neurol., 2001, 49, (3), 345-354.
98. [98] Mir, M.A.; Majee, S.; Das, S.; Dasgupta, D., Association of chromatin with anticancer antibiotics, mithramycin and chromomycin A(3). Bioorg. Med. Chem., 2003, 11, (13), 2791-2801.
99. [99] Gao, Y.; Jia, Z.L.; Kong, X.Y.; Li, Q.; Chang, D.Z.; Wei, D.Y.; Le, X.D.; Huang, S.D.; Huang, S.Y.; Wang, L.W.; Xie, K.P., Combining betulinic acid and mithramycin a effectively suppresses pancreatic cancer by inhibiting proliferation, invasion, and angiogenesis. Cancer Res., 2011, 71, (15), 5182-5193.
100. [100] Garcia, B.; Gonzalez-Sabin, J.; Menendez, N.; Braña, A.F.; Elena Nuñez, L.; Moris, F.; Salas, J.A.; Mendez, C. The chromomycin CmmA acetyltransferase: a membrane-bound enzyme as a tool for increasing structural diversity of the antitumour mithramycin. Microb. Biotechnol., 2011, 4, (2), 226-238.
101. [101] Gonzalez-Sabin, J.; Nunez, L.E.; Brana, A.F.; Mendez, C.; Salas, J.A.; Gotor, V.; Moris, F., Regioselective Enzymatic Acylation of Aureolic Acids to Obtain Novel Analogues with Improved Antitumor Activity. Adv. Synth. Catal., 2012, 354, (8), 1500-1508.
102. [102] Núñez, L.E.; García-Fernández, B.; Pérez, M.; Fernández, A.; Menéndez, N.; González-Sabin, J.; Morís-Varas, F.; Méndez, C.; Salas, J.A. Aureolic acid derivatives, the method for preparation thereof and the uses thereof. U.S. Patent 270,823 A1, October 25, 2012.
103. [103] Gonzalez-Sabin, J.; Nunez, L.E.; Menendez, N.; Brana, A.F.; Mendez, C.; Salas, J.A.; Gotor, V.; Moris, F. Lipase-catalyzed preparation of chromomycin A(3) analogues and biological evaluation for anticancer activity. Bioorg. Med. Chem. Lett., 2012, 22, (13), 4310-4313.
104. [104] Fiaux, H.; Popowycz, F.; Favre, S.; Schutz, C.; Vogel, P.; Gerber-Lemaire, S.; Juillerat-Jeanneret, L., Functionalized Pyrrolidines inhibit alpha-mannosidase activity and growth of human glioblastoma and melanoma cells. J. Med. Chem., 2005, 48, (13), 4237-4246.
105. [105] Zhu, J.J.; Zhou, Y.F.; Wang, G.N.; Tai, G.H.; Ye, X.S. Cell cycle arrest, apoptosis and autophagy induced by iminosugars on K562 cells. Eur. J. Pharmacol., 2014, 731, 65-72.
106. [106] Lu, Y.; Xu, Y.Y.; Fan, K.Y.; Shen, Z.H. 1-deoxymannojirimycin, the alpha 1,2-mannosidase inhibitor, induced cellular endoplasmic reticulum stress in human hepatocarcinoma cell 7721. Biochem. Bioph. Res. Co., 2006, 344, (1), 221-225.
107. [107] Wang, R.-J.; Yang, C.-H.; Hu, M.-L. 1-Deoxynojirimycin inhibits metastasis of B16F10 melanoma cells by attenuating the activity and expression of matrix metalloproteinases-2 and-9 and altering cell surface glycosylation. J. Agric. Food Chem., 2010, 58, (16), 8988-8993.
108. Goti, A.; Cardona, F.; Brandi, A. Improved syntheses of (+)-lentiginosine and (1S,2S,7R,8aS)-trihydroxyoctahydroindolizine by butenol cycloaddition to enantiopure protected dihydroxy pyrroline N-oxides. Synlett, 1996, (8), 761.
109. [109] Brandi, A.; Cicchi, S.; Cordero, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. Assignment of the absolute configuration of natural lentiginosine by synthesis and enzymatic assays of optically pure (+)-enantiomers and (-)-enantiomers. J. Org. Chem., 1995, 60, (21), 6806-6812.
110. [110] Chandra, K.L.; Chandrasekhar, M.; Singh, V.K. Total Synthesis of (-)-and (+)-Lentiginosine. J. Org. Chem., 2002, 67, (13), 4630-4633.
111. [111] Macchi, B.; Minutolo, A.; Grelli, S.; Cardona, F.; Cordero, F.M.; Mastino, A.; Brandi, A. The novel proapoptotic activity of nonnatural enantiomer of Lentiginosine. Glycobiology, 2010, 20, (5), 500-506.
112. [112] Minutolo, A.; Grelli, S.; Marino-Merlo, F.; Cordero, F.M.; Brandi, A.; Macchi, B.; Mastino, A. D(-)lentiginosine-induced apoptosis involves the intrinsic pathway and is p53-independent. Cell Death Dis., 2012, 3.
113. Dal Piaz, F.; Vassallo, A.; Chini, M.G.; Cordero, F.M.; Cardona, F.; Pisano, C.; Bifulco, G.; De Tommasi, N.; Brandi, A. Natural Iminosugar (+)-Lentiginosine Inhibits ATPase and Chaperone Activity of Hsp90. PLoS One, 2012, 7, (8).
114. [114] Ansari, A.A.; Vankar, Y.D. Synthesis of pyrrolidine iminosugars, (-)-lentiginosine, (-)-swainsonine and their 8a-epimers from Dglycals. RSC Adv., 2014, 4, (24), 12555-12567.
115. Akai, S.; Tanimoto, K.; Kanao, Y.; Omura, S.; Kita, Y. Lipasecatalyzed domino kinetic resolution of [small alpha]-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition: a concise asymmetric total synthesis of (-)-rosmarinecine. Chem. Commun., 2005, (18), 2369-2371.
116. [116] Denmark, S.E.; Thorarensen, A.; Middleton, D.S. Tandem [4 + 2]/[3 + 2] Cycloadditions of Nitroalkenes. 9. Synthesis of (-)-Rosmarinecine. J. Am. Chem. Soc., 1996, 118, (35), 8266-8277.
117. [117] Goti, A.; Cacciarini, M.; Cardona, F.; Cordero, F.M.; Brandi, A. Total synthesis of (-)-rosmarinecine by intramolecular cycloaddition of (S)-malic acid derived pyrroline N-oxide. Org. Lett., 2001, 3, (9), 1367-1369.