SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 52, Issue 5, 2013, Pages 1486-1489

A 19F NMR label to substitute polar amino acids in peptides: A CF3-substituted analogue of serine and threonine

(7) Tkachenko, Anton N a,b Mykhailiuk, Pavel K a,b Afonin, Sergii c Radchenko, Dmytro S a Kubyshkin, Vladimir S c Ulrich, Anne S c Komarov, Igor V a

a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV (Ukraine)

b ENAMINE LTD (Ukraine)

c KARLSRUHE INSTITUTE OF TECHNOLOGY (Germany)

Author keywords

amino acids; fluorine; NMR spectroscopy; serine; threonine

Indexed keywords

CYCLOBUTANES; POLAR AMINO ACIDS; SERINE; STRUCTURAL STUDIES; THREONINE;

BUTANE; FLUORINE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES;

AMINO ACIDS;

CYCLOBUTANE DERIVATIVE; DRUG DERIVATIVE; FLUORINE; PEPTIDE; SERINE; THREONINE;

ARTICLE; CHEMISTRY; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CYCLOBUTANES; FLUORINE; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES; SERINE; THREONINE;

MLCS; MLOWN;

EID: 84872862954 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201208069 Document Type: Article

Times cited : (42)

References (50)

1
- 14844344834
- A. S. Ulrich, Prog. Nucl. Magn. Reson. Spectrosc. 2005, 46, 1-21
- (2005) Prog. Nucl. Magn. Reson. Spectrosc. , vol.46 , pp. 1-21
- Ulrich, A.S.¹

2
- 85056024814
- in s (Ed.: A. Ramamoorthy), CRC Press, Boca Raton, FL, p.
- A. S. Ulrich, P. Wadhwani, U. H. N. Dürr, S. Afonin, R. W. Glaser, E. Strandberg, P. Tremouilhac, C. Sachse, M. Berditchevskaia, S. L. Grage, in NMR spectroscopy of biological solid s (Ed.:, A. Ramamoorthy,), CRC Press, Boca Raton, FL, 2006, p. 215-236
- (2006) NMR Spectroscopy of Biological Solid , pp. 215-236
- Ulrich, A.S.¹ Wadhwani, P.² Dürr, U.H.N.³ Afonin, S.⁴ Glaser, R.W.⁵ Strandberg, E.⁶ Tremouilhac, P.⁷ Sachse, C.⁸ Berditchevskaia, M.⁹ Grage, S.L.¹⁰

3
- 77950509966
- S. L. Grage, S. Afonin, A. S. Ulrich, Methods Mol. Biol. 2010, 618, 183-207
- (2010) Methods Mol. Biol. , vol.618 , pp. 183-207
- Grage, S.L.¹ Afonin, S.² Ulrich, A.S.³

4
- 84855935769
- in (Eds.: V. Gouverneur, K. Müller), Imperial College Press, London
- V. S. Kubyshkin, I. V. Komarov, S. Afonin, P. K. Mykhailiuk, S. L. Grage, A. S. Ulrich, in Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications (Eds.:, V. Gouverneur, K. Müller,), Imperial College Press, London, 2012, pp. 91-139
- (2012) Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications , pp. 91-139
- Kubyshkin, V.S.¹ Komarov, I.V.² Afonin, S.³ Mykhailiuk, P.K.⁴ Grage, S.L.⁵ Ulrich, A.S.⁶

5
- 80455158003
- K. Koch, S. Afonin, M. Ieronimo, M. Berditsch, A. S. Urich, Top. Curr. Chem. 2012, 306, 89-118.
- (2012) Top. Curr. Chem. , vol.306 , pp. 89-118
- Koch, K.¹ Afonin, S.² Ieronimo, M.³ Berditsch, M.⁴ Urich, A.S.⁵

6
- 0041525971
- S. Afonin, R. W. Glaser, M. Berditchevskaia, P. Wadhwani, K. H. Gührs, U. Möllmann, A. Perner, A. S. Ulrich, ChemBioChem 2003, 4, 1151-1163
- (2003) ChemBioChem , vol.4 , pp. 1151-1163
- Afonin, S.¹ Glaser, R.W.² Berditchevskaia, M.³ Wadhwani, P.⁴ Gührs, K.H.⁵ Möllmann, U.⁶ Perner, A.⁷ Ulrich, A.S.⁸

7
- 1842783092
- R. W. Glaser, C. Sachse, U. H. N. Dürr, P. Wadhwani, A. S. Ulrich, J. Magn. Reson. 2004, 168, 153-163
- (2004) J. Magn. Reson. , vol.168 , pp. 153-163
- Glaser, R.W.¹ Sachse, C.² Dürr, U.H.N.³ Wadhwani, P.⁴ Ulrich, A.S.⁵

8
- 33646135796
- E. Strandberg, P. Wadhwani, P. Tremouilhac, U. H. N. Dürr, A. S. Ulrich, Biophys. J. 2006, 90, 1676-1686
- (2006) Biophys. J. , vol.90 , pp. 1676-1686
- Strandberg, E.¹ Wadhwani, P.² Tremouilhac, P.³ Dürr, U.H.N.⁴ Ulrich, A.S.⁵

9
- 53549110101
- P. K. Mikhailiuk, S. Afonin, A. N. Chernega, E. B. Rusanov, M. O. Platonov, G. G. Dubinina, M. Berditsch, A. S. Ulrich, I. V. Komarov, Angew. Chem. 2006, 118, 5787-5789
- (2006) Angew. Chem. , vol.118 , pp. 5787-5789
- Mikhailiuk, P.K.¹ Afonin, S.² Chernega, A.N.³ Rusanov, E.B.⁴ Platonov, M.O.⁵ Dubinina, G.G.⁶ Berditsch, M.⁷ Ulrich, A.S.⁸ Komarov, I.V.⁹

10
- 33748543300
- Angew. Chem. Int. Ed. 2006, 45, 5659-5661
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 5659-5661

11
- 74449084822
- P. K. Mykhailiuk, S. Afonin, G. V. Palamarchuk, O. V. Shishkin, A. S. Ulrich, I. V. Komarov, Angew. Chem. 2008, 120, 5849-5851
- (2008) Angew. Chem. , vol.120 , pp. 5849-5851
- Mykhailiuk, P.K.¹ Afonin, S.² Palamarchuk, G.V.³ Shishkin, O.V.⁴ Ulrich, A.S.⁵ Komarov, I.V.⁶

12
- 53549126092
- Angew. Chem. Int. Ed. 2008, 47, 5765-5767.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5765-5767

13
- 0842329183
- S. Afonin, U. H. N. Dürr, R. W. Glaser, A. S. Ulrich, Magn. Reson. Chem. 2004, 42, 195-203
- (2004) Magn. Reson. Chem. , vol.42 , pp. 195-203
- Afonin, S.¹ Dürr, U.H.N.² Glaser, R.W.³ Ulrich, A.S.⁴

14
- 17844363968
- R. W. Glaser, C. Sachse, U. H. N. Dürr, P. Wadhwani, S. Afonin, E. Strandberg, A. S. Ulrich, Biophys. J. 2005, 88, 3392-3397
- (2005) Biophys. J. , vol.88 , pp. 3392-3397
- Glaser, R.W.¹ Sachse, C.² Dürr, U.H.N.³ Wadhwani, P.⁴ Afonin, S.⁵ Strandberg, E.⁶ Ulrich, A.S.⁷

15
- 33750621064
- S. L. Grage, A. V. Suleymanova, S. Afonin, P. Wadhwani, A. S. Ulrich, J. Magn. Reson. 2006, 183, 77-86
- (2006) J. Magn. Reson. , vol.183 , pp. 77-86
- Grage, S.L.¹ Suleymanova, A.V.² Afonin, S.³ Wadhwani, P.⁴ Ulrich, A.S.⁵

16
- 34848867831
- S. Afonin, P. K. Mykhailiuk, I. V. Komarov, A. S. Ulrich, J. Pept. Sci. 2007, 13, 614-623
- (2007) J. Pept. Sci. , vol.13 , pp. 614-623
- Afonin, S.¹ Mykhailiuk, P.K.² Komarov, I.V.³ Ulrich, A.S.⁴

17
- 57549086833
- P. Wadhwani, J. Bürck, E. Strandberg, C. Mink, S. Afonin, A. S. Ulrich, J. Am. Chem. Soc. 2008, 130, 16515-16517
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 16515-16517
- Wadhwani, P.¹ Bürck, J.² Strandberg, E.³ Mink, C.⁴ Afonin, S.⁵ Ulrich, A.S.⁶

18
- 57549112908
- S. Afonin, S. L. Grage, M. Ieronimo, P. Wadhwani, A. S. Ulrich, J. Am. Chem. Soc. 2008, 130, 16512-16514
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 16512-16514
- Afonin, S.¹ Grage, S.L.² Ieronimo, M.³ Wadhwani, P.⁴ Ulrich, A.S.⁵

19
- 39749155818
- E. Strandberg, N. Kanithasen, D. Tiltak, J. Bürck, P. Wadhwani, O. Zwernemann, A. S. Ulrich, Biochemistry 2008, 47, 2601-2616
- (2008) Biochemistry , vol.47 , pp. 2601-2616
- Strandberg, E.¹ Kanithasen, N.² Tiltak, D.³ Bürck, J.⁴ Wadhwani, P.⁵ Zwernemann, O.⁶ Ulrich, A.S.⁷

20
- 70350660660
- D. Maisch, P. Wadhwani, S. Afonin, C. Böttcher, B. Koksch, A. S. Ulrich, J. Am. Chem. Soc. 2009, 131, 15596-15597
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 15596-15597
- Maisch, D.¹ Wadhwani, P.² Afonin, S.³ Böttcher, C.⁴ Koksch, B.⁵ Ulrich, A.S.⁶

21
- 78449307933
- M. Salwiczek, P. K. Mikhailiuk, S. Afonin, I. V. Komarov, A. S. Ulrich, B. Koksch, Amino Acids 2010, 39, 1589-1593
- (2010) Amino Acids , vol.39 , pp. 1589-1593
- Salwiczek, M.¹ Mikhailiuk, P.K.² Afonin, S.³ Komarov, I.V.⁴ Ulrich, A.S.⁵ Koksch, B.⁶

22
- 77954246278
- M. Ieronimo, S. Afonin, K. Koch, M. Berditsch, P. Wadhwani, A. S. Ulrich, J. Am. Chem. Soc. 2010, 132, 8822-8824
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 8822-8824
- Ieronimo, M.¹ Afonin, S.² Koch, K.³ Berditsch, M.⁴ Wadhwani, P.⁵ Ulrich, A.S.⁶

23
- 79956041013
- D. Grasnick, U. Sternberg, E. Strandberg, P. Wadhwani, A. S. Ulrich, Eur. Biophys. J. 2011, 40, 529-543
- (2011) Eur. Biophys. J. , vol.40 , pp. 529-543
- Grasnick, D.¹ Sternberg, U.² Strandberg, E.³ Wadhwani, P.⁴ Ulrich, A.S.⁵

24
- 84858068813
- P. Wadhwani, E. Strandberg, N. Heidenreich, J. Bürck, S. Fanghänel, A. S. Ulrich, J. Am. Chem. Soc. 2012, 134, 6512-6515.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 6512-6515
- Wadhwani, P.¹ Strandberg, E.² Heidenreich, N.³ Bürck, J.⁴ Fanghänel, S.⁵ Ulrich, A.S.⁶

25
- 0029147823
- M. B. Swindells, M. W. MacArthur, J. M. Thornton, Nat. Struct. Biol. 1995, 2, 596-603.
- (1995) Nat. Struct. Biol. , vol.2 , pp. 596-603
- Swindells, M.B.¹ MacArthur, M.W.² Thornton, J.M.³

26
- 77951216021
- G. M. Simon, B. F. Cravatt, J. Biol. Chem. 2010, 285, 11051-11055
- (2010) J. Biol. Chem. , vol.285 , pp. 11051-11055
- Simon, G.M.¹ Cravatt, B.F.²

27
- 80054893675
- Review
- Review:, S. Urban, W. Dickey, Genome Biol. 2011, 12, 231-241.
- (2011) Genome Biol. , vol.12 , pp. 231-241
- Urban, S.¹ Dickey, W.²

28
- 80053437048
- A. Boisramé, A. Cornu, G. Da Costa, M. L. Richard, Eukaryotic Cell 2011, 10, 1317-1330.
- (2011) Eukaryotic Cell , vol.10 , pp. 1317-1330
- Boisramé, A.¹ Cornu, A.² Da Costa, G.³ Richard, M.L.⁴

29
- 0036301006
- J. P. Dawson, J. S. Weinger, D. M. Engelman, J. Mol. Biol. 2002, 316, 799-805
- (2002) J. Mol. Biol. , vol.316 , pp. 799-805
- Dawson, J.P.¹ Weinger, J.S.² Engelman, D.M.³

30
- 33744807250
- B. North, L. Cristian, X. Fu Stowell, J. D. Lear, J. G. Saven, W. F. Degrado, J. Mol. Biol. 2006, 359, 930-939
- (2006) J. Mol. Biol. , vol.359 , pp. 930-939
- North, B.¹ Cristian, L.² Fu Stowell, X.³ Lear, J.D.⁴ Saven, J.G.⁵ Degrado, W.F.⁶

31
- 33750372525
- J. M. Rauceo, R. De Armond, H. Otoo, P. C. Kahn, S. A. Klotz, N. K. Gaur, P. N. Lipke, Eukaryotic Cell 2006, 5, 1664-1673.
- (2006) Eukaryotic Cell , vol.5 , pp. 1664-1673
- Rauceo, J.M.¹ De Armond, R.² Otoo, H.³ Kahn, P.C.⁴ Klotz, S.A.⁵ Gaur, N.K.⁶ Lipke, P.N.⁷

32
- 79959397904
- B. Antonny, Annu. Rev. Biochem. 2011, 80, 101-123
- (2011) Annu. Rev. Biochem. , vol.80 , pp. 101-123
- Antonny, B.¹

33
- 77951896130
- G. Drin, B. Antonny, FEBS Lett. 2010, 584, 1840-1847.
- (2010) FEBS Lett. , vol.584 , pp. 1840-1847
- Drin, G.¹ Antonny, B.²

34
- 84872867978
- ACS, Washington DC
- B. E. Smart, Properties of Fluorinated Organic Compounds. ACS Monograph 187, Vol.1, ACS, Washington DC, 1995
- (1995) Properties of Fluorinated Organic Compounds. ACS Monograph 187, Vol.1
- Smart, B.E.¹

35
- 0034926661
- B. E. Smart, J. Fluorine Chem. 2001, 109, 3-11
- (2001) J. Fluorine Chem. , vol.109 , pp. 3-11
- Smart, B.E.¹

36
- 47749099373
- R. Smits, C. D. Cadicamo, K. Burger, B. Koksch, Chem. Soc. Rev. 2008, 37, 1727-1739
- (2008) Chem. Soc. Rev. , vol.37 , pp. 1727-1739
- Smits, R.¹ Cadicamo, C.D.² Burger, K.³ Koksch, B.⁴

37
- 0000171574
- [Chem. Abstr. 109:55185]
- V. A. Soloshonok, I. I. Gerus, Y. L. Yagupolskii, V. P. Kukhar, Zh. Org. Khim. 1987, 23, 2308-2313 [Chem. Abstr. 109:55185].
- (1987) Zh. Org. Khim. , vol.23 , pp. 2308-2313
- Soloshonok, V.A.¹ Gerus, I.I.² Yagupolskii, Y.L.³ Kukhar, V.P.⁴

38
- 84987505887
- D. Seebach, E. Juaristi, D. D. Miller, C. Schickli, T. Weber, Helv. Chim. Acta 1987, 70, 237-261.
- (1987) Helv. Chim. Acta , vol.70 , pp. 237-261
- Seebach, D.¹ Juaristi, E.² Miller, D.D.³ Schickli, C.⁴ Weber, T.⁵

39
- 38349052965
- T. Kitamoto, S. Marubayashi, T. Yamazaki, Tetrahedron 2008, 64, 1888-1894.
- (2008) Tetrahedron , vol.64 , pp. 1888-1894
- Kitamoto, T.¹ Marubayashi, S.² Yamazaki, T.³

40
- 0001411292
- P. Ballinger, F. A. Long, J. Am. Chem. Soc. 1960, 82, 795-798.
- (1960) J. Am. Chem. Soc. , vol.82 , pp. 795-798
- Ballinger, P.¹ Long, F.A.²

41
- 0001561187
- P. Ballinger, F. A. Long, J. Am. Chem. Soc. 1959, 81, 1050-1053.
- (1959) J. Am. Chem. Soc. , vol.81 , pp. 1050-1053
- Ballinger, P.¹ Long, F.A.²

42
- 67649976811
- D. S. Radchenko, P. K. Mykhailiuk, I. V. Komarov, A. V. Bezdudny, Synlett 2009, 1827-1829.
- (2009) Synlett , pp. 1827-1829
- Radchenko, D.S.¹ Mykhailiuk, P.K.² Komarov, I.V.³ Bezdudny, A.V.⁴

43
- 0006598557
- I. Ruppert, K. Schlich, W. Volbach, Tetrahedron Lett. 1984, 25, 2195-2198.
- (1984) Tetrahedron Lett. , vol.25 , pp. 2195-2198
- Ruppert, I.¹ Schlich, K.² Volbach, W.³

44
- 0031140114
- G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757-786.
- (1997) Chem. Rev. , vol.97 , pp. 757-786
- Prakash, G.K.S.¹ Yudin, A.K.²

45
- 0018812791
- C. D. Chang, M. Waki, M. Ahmad, J. Meienhofer, E. O. Lundell, J. D. Haug, Int. J. Peptide Prot. Res. 1980, 15, 59-66
- (1980) Int. J. Peptide Prot. Res. , vol.15 , pp. 59-66
- Chang, C.D.¹ Waki, M.² Ahmad, M.³ Meienhofer, J.⁴ Lundell, E.O.⁵ Haug, J.D.⁶

46
- 0023411687
- R. C.deL. Milton, E. Becker, S. C. F. Milton, J. E. J. Baxter, J. F. Elsworth, Int. J. Peptide Prot. Res. 1987, 30, 431-432
- (1987) Int. J. Peptide Prot. Res. , vol.30 , pp. 431-432
- De Milton, R.C.L.¹ Becker, E.² Milton, S.C.F.³ Baxter, J.E.J.⁴ Elsworth, J.F.⁵

47
- 0030722620
- D. A. Wellings, E. Atherton, Methods Enzymol. 1997, 289, 44-67.
- (1997) Methods Enzymol. , vol.289 , pp. 44-67
- Wellings, D.A.¹ Atherton, E.²

48
- 85004775207
- D. R. Bolin, I. I. Sytwu, F. Humiec, J. Meienhofer, Int. J. Peptide Prot. Res. 1989, 33, 353-359.
- (1989) Int. J. Peptide Prot. Res. , vol.33 , pp. 353-359
- Bolin, D.R.¹ Sytwu, I.I.² Humiec, F.³ Meienhofer, J.⁴

49
- 14744304016
- A. Giacometti, O. Cirioni, W. Kamysz, G. D′Amato, C. Silvestri, M. S. Del Prete, A. Licci, J. Lukasiak, G. Scalise, J. Antimicrob. Chemother. 2005, 55, 272-274.
- (2005) J. Antimicrob. Chemother. , vol.55 , pp. 272-274
- Giacometti, A.¹ Cirioni, O.² Kamysz, W.³ Damato, G.⁴ Silvestri, C.⁵ Del Prete, M.S.⁶ Licci, A.⁷ Lukasiak, J.⁸ Scalise, G.⁹

50
- 84872840240
- CCDC-890358 (1) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
- CCDC-890358 (1) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.