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Letters in Organic Chemistry

Volumn 5, Issue 6, 2008, Pages 444-449

Lanthanide(III) chelates for selective solution phase labeling of biomolecules

(3) Ketola, Janne a Jaakkola, Lassi a Hovinen, Jari a

a PerkinElmer Finland Oy (Finland)

Author keywords

'Click chemistry'Lanthanide(III) chelates; Labeling; Native chemical ligation; Phosphate elimination

Indexed keywords

EID: 57349116296 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017808785740462 Document Type: Article

Times cited : (3)

References (48)

1
- 0035683339
- For reviews, see: a
- For reviews, see: (a) Hemmilä, I.; Mukkala, V.-M. Crit. Rev. Clin Lab. Sci., 2002, 38, 441
- (2002) Crit. Rev. Clin Lab. Sci , vol.38 , pp. 441
- Hemmilä, I.¹ Mukkala, V.-M.²

2
- 0027227462
- (b) Mathis G. Clin. Chem., 1993, 39, 1953
- (1993) Clin. Chem , vol.39 , pp. 1953
- Mathis, G.¹

3
- 0033368046
- (c) Mathis, G. J. Biomol. Screening, 1999, 4, 309.
- (1999) J. Biomol. Screening , vol.4 , pp. 309
- Mathis, G.¹

4
- 0033370541
- (d) Pope, A.J. J. Biomol. Screen., 1999, 6, 301.
- (1999) J. Biomol. Screen , vol.6 , pp. 301
- Pope, A.J.¹

5
- 0037262667
- Fichna, J.; Janecka, A. Bioconjug. Chem., 2003, 14, 3.
- (2003) Bioconjug. Chem , vol.14 , pp. 3
- Fichna, J.¹ Janecka, A.²

6
- 0036077207
- (a) Peuralahti, J.; Hakala, H.; Mukkala, V.-M.; Hurskainen, P.; Mulari, O.; Hovinen, J. Bioconjug. Chem., 2002, 13, 870
- (2002) Bioconjug. Chem , vol.13 , pp. 870
- Peuralahti, J.¹ Hakala, H.² Mukkala, V.-M.³ Hurskainen, P.⁴ Mulari, O.⁵ Hovinen, J.⁶

7
- 33644790207
- (b) Jaakkola, L.; Peuralahti, J.; Hakala, H.; Hurskainen, P.; Mukkala, V.-M.; Hovinen, J. J. Pept. Sci., 2006, 12, 199.
- (2006) J. Pept. Sci , vol.12 , pp. 199
- Jaakkola, L.¹ Peuralahti, J.² Hakala, H.³ Hurskainen, P.⁴ Mukkala, V.-M.⁵ Hovinen, J.⁶

8
- 0035833682
- Hovinen, J.; Hakala, H. Org. Lett., 2001, 3, 2473
- (2001) Org. Lett , vol.3 , pp. 2473
- Hovinen, J.¹ Hakala, H.²

9
- 0037152546
- (b) Hakala, H.; Ollikka, P.; Degerholm, J.; Hovinen, J. Tetrahedron, 2002, 58, 8771
- (2002) Tetrahedron , vol.58 , pp. 8771
- Hakala, H.¹ Ollikka, P.² Degerholm, J.³ Hovinen, J.⁴

10
- 18844399151
- (c) Jaakkola, L.; Peuralahti, J.; Kunttu, J.; Tallqvist, P.; Mukkala, V.-M.; Hakala, H.; Ylikoski, A.; Hovinen, J. Bioconjug. Chem., 2005, 16, 700.
- (2005) Bioconjug. Chem , vol.16 , pp. 700
- Jaakkola, L.¹ Peuralahti, J.² Kunttu, J.³ Tallqvist, P.⁴ Mukkala, V.-M.⁵ Hakala, H.⁶ Ylikoski, A.⁷ Hovinen, J.⁸

11
- 0035316766
- Ahn, N.G.; Resing, K.A. Nat. Biotechnol., 2001, 19, 317.
- (2001) Nat. Biotechnol , vol.19 , pp. 317
- Ahn, N.G.¹ Resing, K.A.²

12
- 0001426432
- Adam, G.; Sorensen, E.; Gravatt, B. Mol. Cell. Proteomics, 2002, 1.10, 781.
- Adam, G.; Sorensen, E.; Gravatt, B. Mol. Cell. Proteomics, 2002, 1.10, 781.

13
- 0042861519
- Knight, Z.A.; Schilling, B.; Row, R.H.; Kenski, D.M.; Gibson, B.W.; Shokat, K.M. Nat. Biotechnol., 2003, 21, 1047.
- (2003) Nat. Biotechnol , vol.21 , pp. 1047
- Knight, Z.A.¹ Schilling, B.² Row, R.H.³ Kenski, D.M.⁴ Gibson, B.W.⁵ Shokat, K.M.⁶

14
- 0035356565
- Goshe, M.B.; Conrads, T.P.; Panisko, E.A.; Agnell, N.H.; Veenstra, T.D.; Smith, R.D. Anal. Chem., 2001, 73, 2578.
- (2001) Anal. Chem , vol.73 , pp. 2578
- Goshe, M.B.¹ Conrads, T.P.² Panisko, E.A.³ Agnell, N.H.⁴ Veenstra, T.D.⁵ Smith, R.D.⁶

15
- 0032542058
- Jaffe, H.; Veeranna, H.; Pant, H.C. Biochemistry, 1998, 37, 16211.
- (1998) Biochemistry , vol.37 , pp. 16211
- Jaffe, H.¹ Veeranna, H.² Pant, H.C.³

16
- 0034868043
- Adamczyk, M.; Gebler, J.C.; Wu. J. Rapid Communn. Mass Spectrom., 2001, 15, 1481.
- (2001) Rapid Communn. Mass Spectrom , vol.15 , pp. 1481
- Adamczyk, M.¹ Gebler, J.C.² Wu, J.³

17
- 24144459552
- Mattila, K.; Siltainsuu, J.; Balaspiri, L.; Ora, M.; Lönnberg, H. Org. Biomol. Chem., 2005, 3, 3039.
- (2005) Org. Biomol. Chem , vol.3 , pp. 3039
- Mattila, K.¹ Siltainsuu, J.² Balaspiri, L.³ Ora, M.⁴ Lönnberg, H.⁵

18
- 0031234697
- Latva, M.; Takalo, H.; Mukkala, V.-M.; Matachescu, C.; Rodríquez-Ubis, J.-C.; Kankare, J. J. Luminescence, 1997, 75, 149.
- (1997) J. Luminescence , vol.75 , pp. 149
- Latva, M.¹ Takalo, H.² Mukkala, V.-M.³ Matachescu, C.⁴ Rodríquez-Ubis, J.-C.⁵ Kankare, J.⁶

19
- 33645566228
- Hovinen, J. Chem. Biodivers., 2006, 3, 296.
- (2006) Chem. Biodivers , vol.3 , pp. 296
- Hovinen, J.¹

20
- 0000595912
- Volante, R.P. Tetrahedron Lett., 1981, 22, 3119.
- (1981) Tetrahedron Lett , vol.22 , pp. 3119
- Volante, R.P.¹

21
- 0343338078
- Myllymäki, V.T.; Lindvall, M.K.; Koskinen, A.P.M. Tetrahedron, 2001, 57, 4629.
- (2001) Tetrahedron , vol.57 , pp. 4629
- Myllymäki, V.T.¹ Lindvall, M.K.² Koskinen, A.P.M.³

22
- 57349188856
- Synthesis of tetramethyl 2,2′,2″,2‴, 4′-[4-(6- thioacetylhexynyl) phenyl, 2,2″: 6′,2″-terpyridine- 6,6″-diyl]bis(methylenenitrilo, tetrakis Acetate (2, Triphenylphosphine (0.92 g, 3.50 mmol) and diisopropylazodicarboxylate (700 μL, 3.50 mmol) were dissolved in dry THF (35 mL) at 0 °C. Compound 1 (1.75 g, 2.33 mmol) and thioacetic acid (0.25 mL, 3.50 mmol) and were added, and the mixture was stirred at 0 °C for 2 h followed by stirring overnight at RT. All volatiles were removed in vacuo. Purification was performed on silica gel (eluent petroleum ether b.p. 40-60 °C: ethyl acetate: triethylamine; 4:5:1, v/v/v, Yield was 2.8 g (76, 1H-NMR, CDCl3, δ 8.70 (1H, s, 8.55 (2H, d, J 7.7, 7.86 (4H, m, 7.58 (4H, m, 4.19 (4H, s, 3.73 (8H, s, 3.70 (12H, s, 2.96 (2H, t, J 6.8, 2.35 (3H, s, 1.76 4H, m
- 3): δ 8.70 (1H, s); 8.55 (2H, d, J 7.7); 7.86 (4H, m); 7.58 (4H, m); 4.19 (4H, s); 3.73 (8H, s); 3.70 (12H, s); 2.96 (2H, t, J 6.8); 2.35 (3H, s); 1.76 (4H, m).

23
- 57349151425
- Synthesis of 2,2′,2″,2‴, 4′-[4-(6-mercaptohexynyl)phenyl, 2, 2″:6′,2″-terpyridine-6,6″-diyl]bis, methylenenitrilo)}tetrakisacetic acid europium(III, 3, Compound 2 (0.10 g, 0.10 mmol) was dissolved in methanolic potassium hydroxide (20 μL, 0.5 mmol) and the mixture was stirred for 2 h at RT and concentrated. The residue was dissolved in water, and the pH was adjusted to 6.5 with aq. HCl. Europium(III) chloride hexahydrate (55 mg, 0.15 mmol; predissolved in 0.1 mL of water) was slowly added, and the mixture was stirred for 1 h at RT, after which pH was raised to 10 with 0.1 M NaOH. The europium hydroxide formed was removed by centrifugation, and the solvent was removed in vacuo. The residue was dissolved in water (1 mL) and extracted with phenol 0.5 g, The aqueous layer was discharged, and the phenol and the product were partitioned between diethyl ether and water. The aqueous phase was washed with diethyl et
- -: calcd, 860.13; found, 860.12.

24
- 0027944205
- Dawson, P.E.; Muir, T.W.; Clark-Lewis, I.C.; Kent, S.B.H. Science, 1996, 266, 776.
- (1996) Science , vol.266 , pp. 776
- Dawson, P.E.¹ Muir, T.W.² Clark-Lewis, I.C.³ Kent, S.B.H.⁴

25
- 0034637593
- Stetsenko, D. A.; Gait, M. J. Org. Chem., 2000, 65, 4900.
- (2000) J. Org. Chem , vol.65 , pp. 4900
- Stetsenko, D.A.¹ Gait, M.²

26
- 26444474535
- Dose, C.; Seitz, O. Org. Lett., 2005, 7, 4365.
- (2005) Org. Lett , vol.7 , pp. 4365
- Dose, C.¹ Seitz, O.²

27
- 11844283271
- Tolbert, T.J.; Franke, D.; Wong, C.-H. Bioorg. Med. Chem., 2005, 13, 909.
- (2005) Bioorg. Med. Chem , vol.13 , pp. 909
- Tolbert, T.J.¹ Franke, D.² Wong, C.-H.³

28
- 32844462683
- Chen, J.; Warren, J.D.; Wu, B.; Chen, G.; Wan, Q.; Danishefsky, S.J. Tetrahedron Lett., 2006, 47, 1969.
- (2006) Tetrahedron Lett , vol.47 , pp. 1969
- Chen, J.¹ Warren, J.D.² Wu, B.³ Chen, G.⁴ Wan, Q.⁵ Danishefsky, S.J.⁶

29
- 33646899308
- Kushnir, S.; Marsac, Y.; Breitling, R.; Granovsky, I.; Brok-Volchanskaya, V.; Goody, R.S.; Becker, C.F.W.; Alexandrov, K. Bioconjug. Chem., 2006, 17, 610.
- (2006) Bioconjug. Chem , vol.17 , pp. 610
- Kushnir, S.¹ Marsac, Y.² Breitling, R.³ Granovsky, I.⁴ Brok-Volchanskaya, V.⁵ Goody, R.S.⁶ Becker, C.F.W.⁷ Alexandrov, K.⁸

30
- 57349174345
- -): calcd, 1075,24; found 1075, 22.
- -): calcd, 1075,24; found 1075, 22.

31
- 0000096835
- Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Angew. Chem. Int. Ed., 2001, 40, 2004.
- (2004) Angew. Chem. Int. Ed , vol.2001 , pp. 40
- Kolb, H.C.¹ Finn, M.G.² Sharpless, K.B.³

32
- 0348109450
- Kolb, H.C.; Sharpless, K.B. Drug Discov. Today, 2003, 8, 1128.
- (2003) Drug Discov. Today , vol.8 , pp. 1128
- Kolb, H.C.¹ Sharpless, K.B.²

33
- 28844480011
- (a) Joralemon, M.J.; Reilly, R.K.; Hawker, C.J.; Wooley, K.L. J. Am. Chem. Soc., 2005, 127, 16892
- (2005) J. Am. Chem. Soc , vol.127 , pp. 16892
- Joralemon, M.J.¹ Reilly, R.K.² Hawker, C.J.³ Wooley, K.L.⁴

34
- 33746300052
- (b) Sun, E.Y.; Josephson, L.; Weissleder, R. Mol. Imaging, 2006, 5, 122.
- (2006) Mol. Imaging , vol.5 , pp. 122
- Sun, E.Y.¹ Josephson, L.² Weissleder, R.³

35
- 0037462409
- Seo. T.S.; Li, Z.; Ruparel, H.; Ju, J. J. Org. Chem., 2003, 68, 609.
- (2003) J. Org. Chem , vol.68 , pp. 609
- Seo, T.S.¹ Li, Z.² Ruparel, H.³ Ju, J.⁴

36
- 57349194171
- Paul, A.; Bittermann, H.; Grmeiner, P. Tetrahedron, 2006, 62, 8912.
- (2006) Tetrahedron , vol.62 , pp. 8912
- Paul, A.¹ Bittermann, H.² Grmeiner, P.³

37
- 33744925392
- (a) Bouillon, C.; Meyer, A.; Vidal, S.; Jochum, A.; Chevolot, Y.; Cloarec, J.-P.; Praly, J.-P; Vasseur, J.-J.; Morvan, F. J. Org. Chem., 2006, 71, 4700
- (2006) J. Org. Chem , vol.71 , pp. 4700
- Bouillon, C.¹ Meyer, A.² Vidal, S.³ Jochum, A.⁴ Chevolot, Y.⁵ Cloarec, J.-P.⁶ Praly, J.-P.⁷ Vasseur, J.-J.⁸ Morvan, F.⁹

38
- 33748609388
- (b) Gierlich, J.; Burley, G.A.; Gramlich, P.M.E.; Hammond, D.M.; Carell, T. Org. Lett., 2006, 8, 3639
- (2006) Org. Lett , vol.8 , pp. 3639
- Gierlich, J.¹ Burley, G.A.² Gramlich, P.M.E.³ Hammond, D.M.⁴ Carell, T.⁵

39
- 34648813808
- (c) Morvan, F.; Meyer, A.; Jochum, A; Sabin, C.; Chevolot, Y; Imberty, A.; Praly, J.-P.; Vasseur, J.-J.; Souteyrand, E.; Vidal, S. Bioconjug. Chem., 2007, 18, 1637.
- (2007) Bioconjug. Chem , vol.18 , pp. 1637
- Morvan, F.¹ Meyer, A.² Jochum, A.³ Sabin, C.⁴ Chevolot, Y.⁵ Imberty, A.⁶ Praly, J.-P.⁷ Vasseur, J.-J.⁸ Souteyrand, E.⁹ Vidal, S.¹⁰

40
- 33746108240
- Molander, G.A.; Ham, J. Org. Lett., 2006, 8, 2767
- (2006) Org. Lett , vol.8 , pp. 2767
- Molander, G.A.¹ Ham, J.²

41
- 33645880449
- (b) Yap, A.H.; Weinreb, S.M. Tetrahedron Lett., 2006, 47, 3035.
- (2006) Tetrahedron Lett , vol.47 , pp. 3035
- Yap, A.H.¹ Weinreb, S.M.²

42
- 34250652169
- Ketola, J.; Katajisto, J.; Hakala, H.; Hovinen, J. Helv. Chim. Acta, 2007, 90, 607.
- (2007) J. Helv. Chim. Acta , vol.90 , pp. 607
- Ketola, J.¹ Katajisto, J.² Hakala, H.³ Hovinen⁴

43
- 0343807922
- Takalo, H.; Hänninen, E.; Kankare, J. Helv. Chim. Acta, 1993, 76, 877.
- (1993) Helv. Chim. Acta , vol.76 , pp. 877
- Takalo, H.¹ Hänninen, E.² Kankare, J.³

44
- 33947657887
- Hovinen, J. Bioconjug. Chem., 2007, 18, 597.
- (2007) Bioconjug. Chem , vol.18 , pp. 597
- Hovinen, J.¹

45
- 57349101658
- -: calcd, 969.14; found, 969.15.
- -: calcd, 969.14; found, 969.15.

46
- 57349141832
- -1): 2920, 2855, 2118, 1705, 1660, 1531
- -1): 2920, 2855, 2118, 1705, 1660, 1531

47
- 57349154804
- -1): 2927, 2854, 2197, 1717, 1660, 1520, 1370, 1156, 1023.
- -1): 2927, 2854, 2197, 1717, 1660, 1520, 1370, 1156, 1023.

48
- 57349132409
- 2+)/2 705.80, found 705.76.
- 2+)/2 705.80, found 705.76.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.