Synthesis of Modified Purine Nucleosides and Related Compounds Mediated by Adenosine Deaminase (ADA) and Adenylate Deaminase (AMPDA)

Enzo Santaniello; Pierangela Ciuffreda; Laura Alessandrini

doi:10.1055/s-2005-861821

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2005(4): 509-526
DOI: 10.1055/s-2005-861821

REVIEW

Synthesis of Modified Purine Nucleosides and Related Compounds Mediated by Adenosine Deaminase (ADA) and Adenylate Deaminase (AMPDA)

Enzo Santaniello*, Pierangela Ciuffreda, Laura Alessandrini
Dipartimento di Scienze Precliniche LITA Vialba, Università degli Studi di Milano, Via G. B. Grassi, 74 - 20157 Milano, Italy
Fax: +39(02)50319723 ; e-Mail: Enzo.Santaniello@unimi.it;

Further Information

Publication History

Received 1 October 2004
Publication Date:
03 February 2005 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Adenosine deaminase (ADA) and adenylic acid deaminase (AMPDA) are enzymes that catalyze the hydrolytic deamination of various purine nucleosides. In light of recent reports, ADA and AMPDA may be considered as valuable biocatalysts in nucleoside chemistry. Here, they can find many synthetic applications in the transformation of purine nucleosides that are modified in the base or the ribose moiety. Their use can be extended to carbocyclonucleosides or acyclonucleosides as well.

1 Introduction
2 Structure and Catalytic Mechanism of Purine Nucleoside and Nucleotide Deaminases
2.1 Adenosine Deaminase (ADA)
2.2 Adenylate Deaminase (AMPDA)
3 ADA as Biocatalyst
3.1 Nucleosides with Modifications in the Purine Moiety
3.2 Adenosines with Modifications in the Furanose Moiety
3.3 Nucleosides Modified in the Purine and Furanose Moieties
3.4 Carbocyclonucleosides
3.5 Acyclonucleosides
4 AMPDA as Biocatalyst
4.1 Modified Nucleosides
4.2 Carbocyclic and Acyclic Nucleosides
5 Stereochemical Specificity of Deaminating Enzymes
5.1 Synthetic Nucleosides
5.2 Carbocyclic and Acyclic Nucleosides
5.3 Diastereoselectivity of ADA and AMPDA
6 Concluding Remarks

Key words

adenosine deaminase - adenylate deaminase - nucleosides - carbocyclonucleosides - acyclonucleosides

References

1 Zielke CI. Suelter CH. Purine, Purine Nucleoside, and Purine Nucleotide Aminohydrolases, In The Enzymes Vol. 4: Boyer PD. Academic Press; New York: 1971. p.47

Google Scholar
2 Cristalli G. Costanzi S. Lambertucci C. Lupidi G. Vitori S. Volpini R. Camaioni E. Med. Res. Rev. 2001, 21: 105

Crossref Google Scholar
3 Lushchak VI. Biochemistry (Moscow) 1996, 61: 143

Google Scholar
4 Dancer JE. Hughes RG. Lindell SD. Plant Physiol. 1997, 114: 119

Crossref Google Scholar
5 Wilson DK. Quiocho FA. Biochemistry 1993, 32: 1689

Crossref Google Scholar
6 Jones JB. Beck JF. Asymmetric syntheses and resolutions using enzymes, In Applications of biochemical systems in organic chemistry Part I: Jones JB. Sih CJ. Perlman D. John Wiley and Sons; New York: 1976. p.107

Google Scholar
7 Wilson DK. Rudolph FB. Quiocho FA. Science 1991, 252: 1278

Crossref Google Scholar
8 Sharff AJ. Wilson DK. Chang Z. Quiocho FA. J. Mol. Biol. 1992, 226: 917

Crossref Google Scholar
9 Wang Z. Quiocho FA. Biochemistry 1998, 37: 8314

Crossref Google Scholar
10 Kinoshita T. Nishio N. Nakanishi I. Sato A. Fujii T. Acta Crystallogr. Sect. D: Biol. Crystallogr. 2003, D59: 299

Google Scholar
11 Hosmane RS. Hong M. Biochem. Biophys. Res. Commun. 1997, 236: 88

Crossref Google Scholar
12 Marrone TJ. Straatsma TP. Briggs JM. Wilson DK. Quiocho FA. McCammon JA. J. Med. Chem. 1996, 39: 277

Crossref Google Scholar
13 Orozco M. Canela EI. Franco R. J. Org. Chem. 1990, 55: 2630

Crossref Google Scholar
14 Orozco M. Canela EI. Franco R. Eur. J. Biochem. 1990, 188: 155

Crossref Google Scholar
15 Orozco M. Velasco D. Canela EI. Franco R. J. Am. Chem. Soc. 1990, 112: 8221

Crossref Google Scholar
16 Orozco M. Lluis C. Mallol J. Canela EI. Franco R. J. Pharm. Sci. 1990, 79: 133

Crossref Google Scholar
17 Zarubin YP. Ill’icheva IA. Purygin PP. Florent’ev VL. Russ. J. Bioorg. Chem. 2002, 28: 284

Crossref Google Scholar
18 Sideraki V. Mohamedali KA. Wilson DK. Chang Z. Kellems RE. Quiocho FA. Rudolph FB. Biochemistry 1996, 35: 7862

Crossref Google Scholar
19 Sideraki V. Wilson DK. Kurz LC. Quiocho FA. Rudolph FB. Biochemistry 1996, 35: 15019

Crossref Google Scholar
20 Wolfenden R. Wenworth DF. Mitchell GN. Biochemistry 1977, 16: 5071

Crossref Google Scholar
21 Bojack G. Earnshaw CG. Klein R. Lindell SD. Lowinski C. Preuss R. Org. Lett. 2001, 3: 839

Crossref Google Scholar
22 Ferrero M. Gotor V. Chem. Rev. 2000, 100: 4319

Crossref Google Scholar
23 Prasad AK. Trikha S. Parmar VS. Bioorg. Chem. 1999, 27: 135

Crossref Google Scholar
24 Samejima H. Kimura K. Noguchi S. Shimura G. In Enzyme Engineering Vol. 3: Pye EK. Weetall HH. Plenum Press; New York: 1978. p.469

Google Scholar
25 Muzzarelli RAA. Enzyme Microb. Technol. 1980, 2: 177

Crossref Google Scholar
26 Stankiewicz A. Spychala J. Skladanowski A. Zydowo M. Comp. Biochem. Physiol. 1979, 62B: 363

Google Scholar
27 Merkler DJ. Kline PC. Weiss P. Schramm VL. Biochemistry 1993, 32: 12993

Crossref Google Scholar
28 Frieden C. Kurz LC. Gilbert HR. Biochemistry 1980, 19: 5303

Crossref Google Scholar
29 Merkler DJ. Schramm VL. Biochemistry 1993, 32: 5792

Crossref Google Scholar
30 Bolen DW. Fisher JR. Biochemistry 1969, 8: 4239

Crossref Google Scholar
31 Cory JG. Suhadolnik RJ. Biochemistry 1965, 4: 1733

Crossref Google Scholar
32 Wolfenden R. J. Am. Chem. Soc. 1966, 88: 3157

Crossref Google Scholar
33 Chassy BM. Suhadolnik RJ. J. Biol. Chem. 1967, 242: 3655

Google Scholar
34 Johnson JA. Thomas HJ. Schaeffer HJ. J. Am. Chem. Soc. 1958, 80: 699

Crossref Google Scholar
35 Cory JG. Suhadolnik RJ. Biochemistry 1965, 4: 1729

Crossref Google Scholar
36 Bloch A. Robins MJ. McCarthy JR. J. Med. Chem. 1967, 10: 908

Crossref Google Scholar
37 Nair V. Wiechert RJ. Bioorg. Chem. 1980, 9: 423

Crossref Google Scholar
38 Nucleosides and Nucleotides as Antitumor and Antiviral Agents Chu CK. Baker DC. Plenum Press; New York: 1993.

Google Scholar
39 Zemlicka J. Endo T. Nucleosides Nucleotides 1996, 15: 619

Google Scholar
40 Ikehara M. Fukui T. Biochem. Biophys. Acta 1974, 338: 512

Crossref Google Scholar
41 Buenger GS. Nair V. Synthesis 1990, 962

Article in Thieme Connect Google Scholar
42 Shelton MJ. O’Donnell AM. Morse GD. Ann. Pharmacother. 1992, 26: 660

Crossref Google Scholar
43 Maguire MH. Sim MK. Eur. J. Biochem. 1971, 23: 22

Crossref Google Scholar
44 Wanner MJ. Degati PYF. Rodenko B. Koomen GJ. Pure Appl. Chem. 2000, 72: 1705

Google Scholar
45 Robins MJ. Zou R. Hansske F. Wnuk SF. Can. J. Chem. 1997, 75: 762

Crossref Google Scholar
46 Baer HP. Drummond GI. Duncan EL. Mol. Pharmacol. 1966, 2: 67

Google Scholar
47 Weckbecker G. Cory JG. Cancer Res. 1987, 47: 2218

Google Scholar
48 Balzarini J. Robins MJ. Zou R. Herdewijn P. De Clercq E. Biochem. Biophys. Res. Commun. 1987, 145: 277

Crossref Google Scholar
49 Okuyama K. Shibuya S. Hamamoto T. Noguchi T. Biosci., Biotechnol., Biochem. 2003, 67: 989

Crossref Google Scholar
50 Robins MJ. Wilson JS. Madej D. Tyrrell DLJ. Lindmark RJ. Wnuk SF. J. Heterocycl. Chem. 2001, 38: 1297

Crossref Google Scholar
51 Sugiyama T. Schweinberger E. Kazimierczuk Z. Ramzaeva N. Rosemeyer H. Seela F. Chem.-Eur. J. 2000, 6: 369

Google Scholar
52 Maury G. Daiboun T. Elalaoui A. Génu-Dellac C. Périgaud C. Bergogne C. Gosselin G. Imbach J.-L. Nucleosides Nucleotides 1991, 10: 1677

Google Scholar
53 Chae W.-G. Chan TCK. Chang C. Tetrahedron 1998, 54: 8661

Crossref Google Scholar
54 Wnuk SF. Stoeckler JD. Robins MJ. Nucleosides Nucleotides 1994, 13: 389

Google Scholar
55 Ciuffreda P. Loseto A. Alessandrini L. Terraneo G. Santaniello E. Eur. J. Chem. 2003, 4748

Google Scholar
56 Ciuffreda P. Casati S. Santaniello E. Tetrahedron 2000, 56: 3239

Crossref Google Scholar
57 Ciuffreda P. Casati S. Santaniello E. Bioorg. Med. Chem. Lett. 1999, 9: 1577

Crossref Google Scholar
58 Robins MJ. Wilson JS. Hansske F. J. Am. Chem. Soc. 1983, 105: 4059

Crossref Google Scholar
59 Webb RR. Wos JA. Martin JC. Brodfuehrer PR. Nucleosides Nucleotides 1988, 7: 147

Google Scholar
60 Seela F. Kaiser K. Chem. Pharm. Bull. 1988, 36: 4153

Crossref Google Scholar
61 Ciuffreda P. Loseto A. Santaniello E. Tetrahedron 2002, 58: 5767

Crossref Google Scholar
62 Marquez VE. Tseng CKH. Mitsuya H. Aoki S. Kelley JA. Ford H. Roth JS. Broder S. Johns DG. Driscoll JS. J. Med. Chem. 1990, 33: 978

Crossref Google Scholar
63 Tritsch D. Jung PMJ. Burger A. Biellmann JF. Bioorg. Med. Chem. Lett. 2000, 10: 139

Crossref Google Scholar
64 Kohgo S. Yamada K. Kitano K. Iwai Y. Sakata S. Ashida N. Hayakawa H. Nameki D. Kodama E. Matsuoka M. Mitsuya H. Ohrui H. Nucleosides, Nucleotides Nucleic Acids 2004, 23: 671

Crossref Google Scholar
65 Cappellacci L. Barboni G. Palmieri M. Pasqualini M. Grifantini M. Costa B. Martini C. Franchetti P. J. Med. Chem. 2002, 45: 1196

Crossref Google Scholar
66 Sakata S, and Yamada T. inventors; PCT Int. Appl. WO 2002012264. (Yamasa Corp., Jpn)
67 Taj SAS. Gurumurthy P. Suresh R. Narayanan S. Meenakshi SS. Sanghvi YS. Nucleosides, Nucleotides Nucleic Acids 2003, 22: 1327

Crossref Google Scholar
68 Barai VN. Zinchenko AL. Eroshevskaya LA. Zhernosek EV. De Clercq E. Mikhailopulo IA. Helv. Chim. Acta 2002, 85: 1893

Crossref Google Scholar
69 Barai VN. Zinchenko AL. Eroshevskaya LA. Zhernosek EV. Balzarini J. De Clercq E. Mikhailopulo IA. Nucleosides, Nucleotides Nucleic Acids 2003, 22: 751

Crossref Google Scholar
70a Ford H. Siddiqui MA. Driscoll JS. Marquez VE. Kelley JA. Mitsuya H. Shirasaka T. J. Med. Chem. 1995, 38: 1189

Crossref Google Scholar
70b Driscoll JS. Siddiqui MA. Ford H. Kelley JA. Roth JS. Mitsuya H. Tanaka M. Marquez VE. J. Med. Chem. 1996, 39: 1619

Crossref Google Scholar
71 Nair V. Sells TB. Synlett 1991, 753

Article in Thieme Connect Google Scholar
72 Shimada N. Hasegawa S. Saito S. Nishikiori T. Fujii A. Takita T. J. Antibiot. 1987, 40: 1788

Crossref Google Scholar
73 Shortnacy-Fowler AT. Tiwari KN. Montgomery JA. Buckheit RW. Secrist JA. Seela F. Helv. Chim. Acta 1999, 82: 2240

Crossref Google Scholar
74 Borthwick AD. Biggadike K. Tetrahedron 1992, 48: 571

Crossref Google Scholar
75 Gala D. Schumacher DP. Synlett 1992, 61

Article in Thieme Connect Google Scholar
76 Exall AM. Jones MF. Mo C.-L. Myers PL. Paternoster IL. Singh H. Storer R. Weingarten GG. Williamson C. Brodie AC. Cook J. Lake DE. Meerholz CA. Turnbull PJ. Highcock RI. J. Chem. Soc., Perkin Trans. 1 1991, 2467

Crossref Google Scholar
77 Gao H. Mitra AK. Synthesis 2000, 329

Article in Thieme Connect Google Scholar
78 Robbins MJ. Hatfield PW. Can. J. Chem. 1982, 60: 547

Crossref Google Scholar
79 Ogilvie KK. Nguyen-ba N. Gillen MF. Radatus BK. Cheriyan UO. Hanna HR. Smith KO. Galloway KS. Can. J. Chem. 1984, 62: 241

Google Scholar
80 Kim DK. Kim HK. Chae Y.-B. Bioorg. Med. Chem. Lett. 1994, 4: 1309

Crossref Google Scholar
81 Haines D. Tseng C. Marquez VE. J. Med. Chem. 1987, 30: 943

Crossref Google Scholar
82 Phadtare S. Zemlicka J. J. Am. Chem. Soc. 1989, 111: 5925

Crossref Google Scholar
83 Qiu Y. Ksebati MB. Ptak RG. Fan BY. Breitenbach JM. Lin J.-S. Cheng Y.-C. Kern E.-R. Drach JC. Zemlicka J. J. Med. Chem. 1998, 41: 10

Crossref Google Scholar
84 Phadtare S. Kessel D. Corbett TH. Renis HE. Court BA. Zemlicka J. J. Med. Chem. 1991, 34: 421

Crossref Google Scholar
85 Xu Z.-Q. Qiu Y.-L. Chokekijchai S. Mitsuya H. Zemlicka J. J. Med. Chem. 1995, 38: 875

Crossref Google Scholar
86 Phadtare S. Zemlicka J. Tetrahedron Lett. 1990, 31: 43

Crossref Google Scholar
87 Phadtare S. Zemlicka J. J. Med. Chem. 1987, 30: 437

Crossref Google Scholar
88 Brakta M. Murthy D. L’Ouverture E. Phadtare S. Bioorg. Med. Chem. Lett. 2002, 12: 1489

Crossref Google Scholar
89 Margolin AL. Borcherding DR. Wolf-Kugel D. Margolin N. J. Org. Chem. 1994, 59: 7214

Crossref Google Scholar
90 Jones BCNM. Zemlicka J. Bioorg. Med. Chem. Lett. 1995, 15: 1633

Google Scholar
91 Pelicano H. Pierra C. Eriksson S. Gosselin G. Imbach J.-L. Maury G. J. Med. Chem. 1997, 40: 3969

Crossref Google Scholar
92 Chun BK. Olgen S. Hong JH. Newton MG. Chu CK. J. Org. Chem. 2000, 65: 685

Crossref Google Scholar
93 Van Draanen NA. Koszalka GW. Nucleosides Nucleotides 1994, 13: 1679

Google Scholar
94 Secrist JA. Montgomery JA. Shealy YF. O’Dell CA. Clayton SJ. J. Med. Chem. 1987, 30: 746

Crossref Google Scholar
95 Vince R. Brownell J. Biochem. Biophys. Res. Commun. 1990, 168: 912

Crossref Google Scholar
96 Borthwich AD, Biggadike K, Kirk BE, Storer R, Weir NG, Baxter AD, and Mo CL. inventors; Eur. Pat. Appl. 0410660.
97 Yoshimura Y. Moon HR. Choi Y. Marquez VE. J. Org. Chem. 2002, 67: 5938

Crossref Google Scholar
98 Hernandez S. Ford H. Marquez VE. Bioorg. Med. Chem. 2002, 10: 2723

Crossref Google Scholar
99 Marquez VE. Russ P. Alonso R. Siddiqui MA. Hernandez S. George C. Nicklaus MC. Dai F. Ford H. Helv. Chim. Acta 1999, 82: 2119

Crossref Google Scholar
100 Rodriguez JB. Marquez VE. Nicklaus MC. Mitsuya H. Barchi JJ. J. Med. Chem. 1994, 37: 3389

Crossref Google Scholar
101 Moon HR. Ford H. Marquez VE. Org. Lett. 2000, 2: 3793

Crossref Google Scholar
102 Qiu Y.-L. Ksebati MB. Zemlicka J. Nucleosides Nucleotides 2000, 19: 31

Google Scholar
103 Zhou S. Breitenbach JM. Borysko KZ. Drach JC. Kern ER. Gullen E. Cheng Y.-C. Zemlicka J. J. Med. Chem. 2004, 47: 566

Crossref Google Scholar
104 Jones BCNM. Drach JC. Corbett TH. Kessel D. Zemlicka J. J. Org. Chem. 1995, 60: 6277

Crossref Google Scholar
105 Guan H.-P. Ksebati MB. Cheng Y.-C. Drach JC. Kern ER. Zemlicka J. J. Org. Chem. 2000, 65: 1280

Crossref Google Scholar
106 Shuto S. Obara T. Yaginuma S. Matsuda A. Chem. Pharm. Bull. 1997, 45: 138

Crossref Google Scholar
107 Ciuffreda P. Loseto A. Santaniello E. Tetrahedron: Asymmetry 2002, 13: 239

Crossref Google Scholar
108 Ciuffreda P. Loseto A. Santaniello E. Tetrahedron: Asymmetry 2004, 15: 203

Crossref Google Scholar