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Synthesis 2002(13): 1781-1801
DOI: 10.1055/s-2002-33907
DOI: 10.1055/s-2002-33907
REVIEW
© Georg Thieme Verlag Stuttgart · New YorkSynthetic Tritium Labeling: Reagents and Methodologies
Further Information
Received
15 April 2002
Publication Date:
09 September 2002 (online)
Publication History
Publication Date:
09 September 2002 (online)
Abstract
This review presents a survey of new high specific activity tritium labeling reagents and methodologies developed in recent years and their applications to tritium labeling chemistry. The review is organized on the basis of reagent type, its development and applications. Emphasis is placed on the synthetic applications of the reagents and techniques that have an exceptionally high capability to produce high specific activity tritium labeled compounds. The focus of this review is on chemical labeling syntheses and does not include heterogeneous/homogeneous metal-catalyzed hydrogen-tritium exchange and biochemical reactions.
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1 Introduction
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2 Synthesis and Applications of Tritiated Hydrides
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2.1 Lithium, Sodium, and Potassium Borotritide Reagents (LiBT4, NaBT4, KBT4)
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2.2 Lithium Tritide (LiT)
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2.3 Lithium Supertritide (LiEt3BT)
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2.4 Lithium Aluminum Tritide (LiAlT4)
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2.5 Lithium Selectride [Li(sec-Bu)3BT]
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2.6 Lithium Trimethoxyborotritide [Li(OCH3)3BT]
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2.7 Tritiated [2-(1,3-Dithianyl)]myrtanylborane (MDBT2)
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2.8 Tritiated Methylborane (CH3BT2)
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2.9 Tritiated Lithium 9-Boratabicyclo[3.3.1]nonane
(Li9-BBNT) -
2.10 Tritiated BoraneTHF Complex (BT3THF)
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2.11 Lithium Borotritide (LiBT4)
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2.12 Tritiated Schwartz’ Reagent (ZrCp2ClT)
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2.13 Tritiated Silanes
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2.14 Tributyltin tritide (Bu3SnT)
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2.15 Tritiated Triacetoxy Sodium Borotritide [NaBT(OAc)3]
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3 Synthesis and Applications of Tritiated Water
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3.1 Tritiated Water (T2O)
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3.2 Tritiated Methylene Diiodide (CHTI2)
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3.3 Tritiated Diimide (TN=NT)
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3.4 Tritioolefination
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3.5 Base-Induced Tritiodesilylation
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3.6 Fluoride-Induced Tritiodesilylation
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3.7 Tritiated Diazomethane (CHTN2)
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4 Catalytic Tritiations with Tritium Gas
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4.1 Catalytic Tritiodehalogenation
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4.2 Heterogeneous Catalytic Tritiations
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4.3 Homogeneous Catalytic Tritiations
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5 Tritium Labeling via Organometallic Compounds
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5.1 Metallation/Reduction with Tritium Gas
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5.2 Metallation/Reduction with Tritiated Water
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6 Conclusion
Key words
tritiated hydrides - heterogeneous catalytic tritiations - high specific activity -
- 2a
Allen J. Isot. Phys. Biomed. Sci. Vol. 1 Labelled Compounds (Part A):Buncel E.Jones JR. Elsevier; Amsterdam: 1987. p.425Reference Ris Wihthout Link - 2b
Andres H,Morimoto H, andWilliams PG. inventors; US Patent 5,186,868.Reference Ris Wihthout Link - 3
Evans EA. Tritium and Its Compounds 2nd ed.: Butterworths; London: 1974. p.14-15Reference Ris Wihthout Link - 4
Evans EA.Warrell DC.Elvidge JA.Jones JR. Handbook of Tritium NMR Spectroscopy and Applications John Wiley and Sons; Chichester: 1985. p.23-24Reference Ris Wihthout Link - 5
Than C.Morimoto H.Andres H.Williams PG. J. Labelled Compd. Radiopharm. 1996, 38: 693 - 6
Zippi EM.Andres H.Morimoto H.Williams PG. Synth. Commun. 1995, 25: 2685 - 7
Andres H.Morimoto H.Williams PG. J. Chem. Soc., Chem. Commun. 1990, 627 - 8
Andres H.Morimoto H.Williams PG. Proceedings of the 4th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1991Buncel E.Kabalka GW. Elsevier; Amsterdam: 1992. p.40Reference Ris Wihthout Link - 9
Andres H,Morimoto H, andWilliams PG. inventors; US Patent 5,186,868.Reference Ris Wihthout Link - 10
Andres H.Morimoto H.Williams PG.Zippi EM. Proceedings of the 5th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1994Allen J.Voges R. John Wiley and Sons; Chichester: 1995. p.83Reference Ris Wihthout Link - 11
Andres H.Than C.Morimoto H.Williams PG. Proceedings of the 6th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1997Heys JR.Melillo DG. John WiIey and Sons Ltd; Chichester: 1998. p.213Reference Ris Wihthout Link - 12
Coates RM.Hegde S.Pearce CJ. Proceedings of the International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1982Duncan WP.Susan AB. Elsevier; Amsterdam: 1983. p.429Reference Ris Wihthout Link - 13
Hegde S.Coates RM.Pearce CJ. J. Chem. Soc., Chem. Commun. 1983, 1484 - 14
Priestley ND.Floss HG.Froland WA.Lipscomb JD.Williams PG.Morimoto H. J. Am. Chem. Soc. 1992, 114: 7561 - 15
Nguyen H.-HAT.Zhu M.Elliott SJ.Nakagawa KH.Hedman B.Costello AM.Peeples TL.Wilkinson B.Morimoto H.Williams PG.Floss HG.Lidstrom ME.Hodgson KO.Chan SI. Proceedings of the 8th International Symposium on Microbial Growth on C1 Compounds, Lidstrom M. E., Tabita F. R. Kluwer Academic Publishers; Dordrecht: 1996. p.150Reference Ris Wihthout Link - 16
Wilkinson B.Zhu M.Priestley ND.Nguyen H.-HT.Morimoto H.Williams PG.Chan SI.Floss HG. J. Am. Chem. Soc. 1996, 118: 92 - 17
Valentine AM.Wilkinson B.Liu KE.Komar-Panicucci S.Priestley ND.Williams PG.Morimoto H.Floss HG.Lippard SJ. J. Am. Chem. Soc. 1997, 119: 1818 - 18
Liu Y.-Y.Thom E.Burger W. Proceedings of the 5th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds 1994Allen J.Voges R. John Wiley and Sons; Chichester: 1995. p.93Reference Ris Wihthout Link - 19
Olah GA.Ohannesian L.Arvangaghi M. Chem. Rev. 1987, 87: 671 - 20
Freer RJ.Day AR.Muthukumaraswamy N.Pinon D.Wu A.Showell HJ.Becker EL. Biochemistry 1982, 21: 257 - 21
Strazzolini P.Giumanini AG.Cauci S. Tetrahedron 1990, 46: 1081 - 22
Montgomery JA.Thomas J. J. Labelled Compd. Radiopharm. 1978, 15: 727 - 23
Burr JG.Brown WG.Heller HE. J. Am. Chem. Soc. 1950, 72: 2560 - 24
Saljoughian M.Williams PG. Curr. Pharm. Des. 2000, 6: 1029 - 25
Dischino DD.Combrink KD.Doweyko L.Morimoto H.Pearce BC.Williams PG.Yevich JP. J. Labelled Compd. Radiopharm. 1995, 36: 789 - 26
Burgos A.Kamenka J.-M.Moustier A.-M.Rousseau B. J. Labelled Compd. Radiopharm. 1991, 29: 1061 - 27
Lamotte H.Degeilh F.Neau P.Ripoche P.Rousseau B. J. Labelled Compd. Radiopharm. 1994, 34: 289 - 28
Saljoughian M.Morimoto H.Williams PG. Fusion Technol. 1992, 21: 318 - 29
Liu Y.-Y.Chen L. J. Labelled Compd. Radiopharm. 1995, 38: 71 - 30
Lee S.Morimoto H.Williams PG. J. Labelled Compd. Radiopharm. 1997, 39: 461 - 31
Burgos A.Kamenka J.-M.Rousseau B. J. Labelled Compd. Radiopharm. 1991, 29: 1347 - 32
Rasset C.Rousseau B. Proceedings of the 5th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds 1994Allen J.Voges R. John Wiley and Sons; Chichester: 1995. p.91Reference Ris Wihthout Link - 33
Rasset C.Rousseau B. J. Labelled Compd. Radiopharm. 1994, 34: 523 - 34
Garmestani K.Link JM.Krohn KA. J. Labelled Compd. Radiopharm. 1990, 28: 1171 - 35
Than C.Morimoto H.Andres H.Williams PG. J. Org. Chem. 1995, 60: 7503 - 36
Than C.Morimoto H.Andres H.Williams PG. J. Org. Chem. 1996, 61: 8771 - 37
Latli B.Than C.Morimoto H.Williams PG.Casida JE. J. Labelled Compd. Radiopharm. 1996, 38: 971 - 38
Huguenin PN.Shimma N. J. Labelled Compd. Radiopharm. 1996, 38: 999 - 39
Dischino DD.Meanwell NA.Morimoto H.Pearce BC.Than C.Torri AF.Williams PG.Yu K.-L. J. Labelled Compd. Radiopharm. 1999, 42: 1061 - 40
Zippi EM.Andres H.Morimoto H.Williams PG. Synth. Commun. 1994, 24: 1037 - 41
Neu H.Andres H. J. Labelled Compd. Radiopharm. 1999, 42: 992 - 42
Kuivila HG. Synthesis 1970, 499 - 43
Neumann WP. Synthesis 1987, 665 - 44
Parnes H.Pease J. J. Org. Chem. 1979, 44: 151 - 45
Miura K.Ichinose Y.Nozaki K.Fugami K.Oshima K.Utimoto K. Bull. Chem. Soc. Jpn. 1989, 62: 143 - 46
Four P.Guibé F. J. Org. Chem. 1981, 46: 4439 - 47
Padwa A.Nimmesgern H.Wong GSK. Tetrahedron Lett. 1985, 26: 957 - 48
Korth HG.Sustmann R.Gröninger KS.Leisung M.Giese B. J. Org. Chem. 1988, 53: 4364 - 49
Barton DHR.McCombie SW. J. Chem. Soc., Perkin Trans. 1 1975, 1574 - 50
Robins MJ.Wilson JS. J. Am. Chem. Soc. 1981, 103: 932 - 51
Jaiswal DK.Andres H.Morimoto H.Williams PG. J. Chem. Soc., Chem. Commun. 1993, 907 - 52
Sugiura S.Tanaka T.Bannai K.Kurozumi S. J. Labelled Compd. Radiopharm. 1991, 29: 1041 - 53
Zippi EM.Plourde GW.Satyamurthy N. J. Labelled Compd. Radiopharm. 1995, 36: 361 - 54
Saljoughian M.Morimoto H.Williams PG.Than C.Seligman SJ. J. Org. Chem. 1996, 61: 9625 - 55
Wichmann J.Huguenin P.Adam G. J. Labelled Compd. Radiopharm. 2000, 43: 1 - 56
Robins MJ.Wilson JS.Hansske F. J. Am. Chem. Soc. 1983, 105: 4059 - 57
Saljoughian M.Morimoto H.Than C.Williams PG. Proceedings of the 6th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1997Heys JR.Melillo DG. John WiIey and Sons; Chichester: 1998. p.193Reference Ris Wihthout Link - 58
Saljoughian M.Morimoto H.Than C.Williams PG.Andres H. J. Labelled Compd. Radiopharm. 1998, 41: 1027 - 59
Ono N.Kaji A. Synthesis 1986, 693 - 60
Barton DHR.Bringmann G.Lamotte G.Motherwell WB.Motherwell RSH.Porter AEA. J. Chem. Soc., Perkin Trans. 1 1980, 2657 - 61
Moenius T.Andres H.Acemoglu M.Kohler B.Schnelli P.Zueger C. J. Labelled Compd. Radiopharm. 2000, 43: 113 - 62
Curran DP.Kim D.Liu HT.Shen W. J. Am. Chem. Soc. 1988, 110: 5900 - 63
Curran DP.Somayajula KV.Yu H. Tetrahedron Lett 1992, 33: 2295 - 64
Than C.Morimoto H.Williams PG.Chehade KAH.Andres DA.Spielmann HP. J. Org. Chem. 2001, 66: 3602 - 65
Jaiswal DK.Morimoto H.Saljoughian M.Williams PG. Proceedings of the 4th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1991Buncel E.Kabalka GW. Elsevier; Amsterdam: 1992. p.46Reference Ris Wihthout Link - 66
Saljoughian M.Morimoto H.Williams PG.DeMello N. J. Chem. Soc., Chem. Commun. 1990, 1652 - 67
Saljoughian M.Williams PG.Morimoto H.Goodlett DR.Van Breemen RB. J. Chem. Soc., Chem. Commun. 1993, 414 - 68
Culf AS.Morimoto H.Williams PG.Lockley WJS.Primrose WU.Jones JR. J. Labelled Compd. Radiopharm. 1996, 38: 373 - 69
Saljoughian M.Morimoto H.Than C.Williams PG. Tetrahedron Lett. 1996, 37: 2923 - 70
Jaiswal DK.Morimoto H.Saljoughian M.Williams PG. Proceedings of the 4th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1991Buncel E.Kabalka GW. Elsevier; Amsterdam: 1992. p.46Reference Ris Wihthout Link - 71
Brook AG. Acc. Chem. Res. 1974, 7: 77 - 72
Brook AG.Warner CM.Limburg WW. Can. J. Chem. 1967, 45: 1231 - 73
Kessar SV. Pure Appl. Chem. 1990, 62: 1397 - 74
Pizey JS. N-Bromosuccinimide, Diazomethane, Manganese Dioxide, Raney Nickel in Synthetic Reagents Vol. 2: Ellis Horwood Ltd; Chichester: 1974. p.65Reference Ris Wihthout Link - 75
Wurdeman RL.Church KM.Gold B. J. Am. Chem. Soc. 1989, 111: 6408 - 76
Gutsche CD. The Reaction of Diazomethane and its Derivatives with Aldehydes and Ketones in Organic Reactions Vol. 8: John Wiley and Sons; Chichester: 1954. p.364Reference Ris Wihthout Link - 77
Black TH. Aldrichimica Acta 1983, 16: 3 - 78
Saljoughian M.Morimoto H.Rapoport H. Proceedings of the 3rd International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1988Baillie TA.Jones JR. Elsevier; Amsterdam: 1989. p.517Reference Ris Wihthout Link - 79
Saljoughian M.Morimoto H.Williams PG. J. Chem. Soc., Perkin Trans. 1 1990, 1803 - 80
Williams PG.Morimoto H.Saljoughian M.Andres H. Trans. Am. Nucl. Soc. 1989, 60: 34 - 81
Jaiswal DK.Morimoto H.Trump EL.Williams PG.Wemmer DE. J. Labelled Compd. Radiopharm. 1996, 38: 743 - 82
Highsmith S.Kubinec M.Jaiswal DK.Morimoto H.Williams PG.Wemmer DE. J. Biomol. NMR 1993, 3: 325 - 83
Jaiswal DK.Morimoto H.Williams PG.Wemmer DE. Proceedings of the 4th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1991Buncel E.Kabalka GW. Elsevier; Amsterdam: 1992. p.448Reference Ris Wihthout Link - 84
Saljoughian M.Morimoto H.Williams PG.Rapoport H. Trans. Am. Nucl. Soc. 1987, 55: 39 - 85
Saljoughian M.Morimoto H.Williams PG.Rapoport H. J. Labelled Compd. Radiopharm. 1988, 25: 313 - 86
O’Neil JP.VanBrocklin HF.Morimoto H.Williams PG. J. Labelled Compd. Radiopharm. 1997, 39: 215 - 87
Callaway JC.Morimoto H.Gynther J.Airaksinen MM.Williams PG. J. Labelled Compd. Radiopharm. 1992, 31: 355 - 88
Kovalainen JT.Morimoto H.Williams PG.Vepsalainen J.Reijonen A.Gynther J. J. Labelled Compd. Radiopharm. 1995, 36: 1147 - 89
Bennani YL.Boehm MF. J. Org. Chem. 1995, 60: 1195 - 90
Hammadi A.Meunier G.Tarride J.-L.Menez A.Genet R. Proceedings of the 6th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1997Heys JR.Melillo DG. John WiIey and Sons Ltd; Chichester: 1998. p.197Reference Ris Wihthout Link - 91
Prestwich GD.Wawrzenczyk C. Proc. Natl. Acad. Sci. U.S.A. 1985, 82: 5290 - 92
Seltzman HH.Odear DF.Laudeman CP.Ivy Carroll F.Wyrick CD. J. Labelled Compd. Radiopharm. 1994, 24: 367 - 93
Taylor R. Tetrahedron Lett. 1975, 435 - 94
Blackburn GM.Flavell AJ.Orgee L.Will JP.Williams GM. J. Chem. Soc., Perkin Trans. 1 1981, 3196 - 95
Rapkin E.Steele G.Schavey R. Am. Lab. 1995, 27: 31 - 96
Pfanner K.Zeller A. J. Labelled Compd. Radiopharm. 1998, 41: 1033 - 97
Lockley WJS. J. Labelled Compd. Radiopharm. 1987, 24: 1509 - 98
Kingston LP.Lockley WJS.Mather AN.Wilkinson DJ.Hesk D.Jones JR. Proceedings of the 5th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds, 1994Allen J.Voges R. John Wiley and Sons; Chichester: 1995. p.57Reference Ris Wihthout Link - 99
Morimoto H.Williams PG. Fusion Technol. 1992, 21: 256
References
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