SCOPUS 정보 검색 플랫폼

Helvetica Chimica Acta

Volumn 89, Issue 4, 2006, Pages 731-746

Synthesis of enniatin-like cyclic depsipeptides via 'direct amide cyclization'

(3) Köttgen, Peter a Linden, Anthony a Heimgartner, Heinz a

a UNIVERSITY OF ZURICH (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; AROMATIC HYDROCARBONS; HYDROCHLORIC ACID; SYNTHESIS (CHEMICAL); TOLUENE; X RAY CRYSTALLOGRAPHY;

CYCLODEPSIPEPTIDES; DIRECT AMIDE CYCLIZATION; LINEAR PRECURSORS;

NITROGEN COMPOUNDS;

1 [1 [(DIMETHYLCARBAMOYL)CYCLOPENTYL]CARBAMOYL] 2 PHENYLETHYL 1 [[2 [1 [[( 2 HYDROXYPROPANOYL)AMINO]CYCLOPENTYL]CARBONYLOXY] 3 PHENYLPROPANOYL]AMINO]CYCLOPENTANE 1 CARBOXYLATE; 1 [[1 (DIMETHYLCARBAMOYL)CYCLOPENTYL]CARBAMOYL] 2 PHENYLETHYL 1 [[2 [1 [[(2 HYDROXY 3 PHENYLPROPANOYL)AMINO]CYCLOPENTYL]CARBONYLOXY] 3 PHENYLPROPANOYL]AMINO]CYCLOPENTANE 1 CARBOXYLATE; 1 [[1 [[ 1 [[1 (DIMETHYLCARBAMOYL) 1 METHYLETHYL]CARBAMOYL] 2 PHENYLETHOXY]CARBONYL] 1 METHYLETHYL]CARBAMOYL] 2 PHENYLETHYL 2 [(2 HYDROXYACETYL)AMINO] 2 METHYLPROPANOATE; 2 HYDROXYACID; 3,9,15, TRIBENZYL 3,9,15 TRIMETHYL 1,7,13 TRIOXA 4,10,16 TRIAZACYCLOOCTADECANE 2,5,8,11,1,4,17 HEXAONE; 6,12 DIBENZYL 18 METHYL 3,3,9,9,15,15 TRIS(TETRAMETHYLENE) 1,7,13 TRIOXA 4,10,16 TRIAZACYCLOOCTADECANE 2,5,8,11,14,17 HEXAONE; 6,12 DIBENZYL 3,3,9,9,15,15 HEXAMETHYL 1,7,13 TRIOXA 4,10,16 TRIAZACYCLOOCTADECANE 2,5,8,11,14,17 HEXAONE; 6,12,18 TRIBENZYL 3,3,9,9,15,15 HEXAMETHYL 1,7,13 TRIOXA 4,10,16 TRIAZACYCLOOCTADECANE 2,5,8,11,14,17 HEXAONE; 6,12,18 TRIBENZYL 3,3,9,9,15,15 TRIS(TETRAMETHYLENE) 1,7,13 TRIOXA 4,10,16 TRIAZACYCLOOCTADECANE 2,5,8,11,14,17 HEXAONE; [[1 [[[1 (DIMETHYLCARBAMOYL) 1 METHYL 2 PHENYLETHYL]CARBAMOYL]METHOXYCARBONYL] 1 METHYL 2 PHENYLETHYL]CARBAMOYL]METHYL 2 [(2 HYDROXYACETYL)AMINO] 2 METHYL 3 PHENYLPROPANOATE; AMINO ACID DERIVATIVE; AZIRINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLODEPSIPEPTIDE; ENNIATIN; OXAZOLONE; PROPIONIC ACID DERIVATIVE; PROTEIN PRECURSOR; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; MACROLACTONIZATION; MICROCRYSTALLINE SUSPENSION; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 33646239823 PISSN: 0018019X EISSN: None Source Type: Journal
DOI: 10.1002/hlca.200690069 Document Type: Article

Times cited : (18)

References (61)

1
- 0029785860
- K. W. Li, J. Wu, W. Xing, J. A. Simpson, J. Am. Chem. Soc. 1996, 118, 7237.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 7237
- Li, K.W.¹ Wu, J.² Xing, W.³ Simpson, J.A.⁴

2
- 0000810802
- Y. Hirai, K. Yokota, T. Momose, Heterocycles 1994, 39, 603.
- (1994) Heterocycles , vol.39 , pp. 603
- Hirai, Y.¹ Yokota, K.² Momose, T.³

3
- 0027499883
- S. Cerrini, E. Gavuzzo, G. Luisi, F. Pinnen, Int. J. Pept. Protein Res. 1993, 41, 282.
- (1993) Int. J. Pept. Protein Res. , vol.41 , pp. 282
- Cerrini, S.¹ Gavuzzo, E.² Luisi, G.³ Pinnen, F.⁴

4
- 0031023054
- A. M. Sefler, M. C. Kozlowski, T. Guo, P. A. Bartlett, J. Org. Chem. 1977, 62, 93.
- (1977) J. Org. Chem. , vol.62 , pp. 93
- Sefler, A.M.¹ Kozlowski, M.C.² Guo, T.³ Bartlett, P.A.⁴

5
- 0030054088
- Y. L. Dory, J. M. Mellor, J. F. McAleer, Tetrahedron Lett. 1996, 52, 1343.
- (1996) Tetrahedron Lett. , vol.52 , pp. 1343
- Dory, Y.L.¹ Mellor, J.M.² McAleer, J.F.³

6
- 0028256250
- T. Imaeda, Y. Hamada, T. Shioiri, Tetrahedron Lett. 1994, 35, 591.
- (1994) Tetrahedron Lett. , vol.35 , pp. 591
- Imaeda, T.¹ Hamada, Y.² Shioiri, T.³

7
- 0041475925
- J. S. Davies, J. Peptide Sci. 2003, 9, 471.
- (2003) J. Peptide Sci. , vol.9 , pp. 471
- Davies, J.S.¹

8
- 0004153150
- Springer, New York
- G. E. Schulz, R. H. Schirmer, 'Principles of Protein Structure', Springer, New York, 1979.
- (1979) Principles of Protein Structure
- Schulz, G.E.¹ Schirmer, R.H.²

9
- 84986356263
- D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1984, 67, 526.
- (1984) Helv. Chim. Acta , vol.67 , pp. 526
- Obrecht, D.¹ Heimgartner, H.²

10
- 84987594022
- D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1987, 70, 329.
- (1987) Helv. Chim. Acta , vol.70 , pp. 329
- Obrecht, D.¹ Heimgartner, H.²

11
- 84987539080
- D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1990, 73, 221.
- (1990) Helv. Chim. Acta , vol.73 , pp. 221
- Obrecht, D.¹ Heimgartner, H.²

12
- 0031008773
- J. M. Villagordo, H. Heimgartner, Helv. Chim. Acta 1997, 80, 748.
- (1997) Helv. Chim. Acta , vol.80 , pp. 748
- Villagordo, J.M.¹ Heimgartner, H.²

13
- 0033972771
- K. N. Koch, A. Linden, H. Heimgartner, Helv. Chim. Acta 2000, 83, 233.
- (2000) Helv. Chim. Acta , vol.83 , pp. 233
- Koch, K.N.¹ Linden, A.² Heimgartner, H.³

14
- 0035901366
- K. N. Koch, A. Linden, H. Heimgartner, Tetrahedron 2001, 57, 2311.
- (2001) Tetrahedron , vol.57 , pp. 2311
- Koch, K.N.¹ Linden, A.² Heimgartner, H.³

15
- 0033838976
- K. N. Koch, H. Heimgartner, Helv. Chim. Acta 2000, 83, 1881.
- (2000) Helv. Chim. Acta , vol.83 , pp. 1881
- Koch, K.N.¹ Heimgartner, H.²

16
- 0035089382
- K. N. Koch, G. Hopp, A. Linden, K. Moehle, H. Heimgartner, Helv. Chim. Acta 2001, 84, 502.
- (2001) Helv. Chim. Acta , vol.84 , pp. 502
- Koch, K.N.¹ Hopp, G.² Linden, A.³ Moehle, K.⁴ Heimgartner, H.⁵

17
- 0033367708
- H. Heimgartner, F. S. Arnhold, S. P. Fritschi, K. N. Koch, J. E. F. Magirius, A. Linden, J. Heterocycl. Chem. 1999, 36, 1539.
- (1999) J. Heterocycl. Chem. , vol.36 , pp. 1539
- Heimgartner, H.¹ Arnhold, F.S.² Fritschi, S.P.³ Koch, K.N.⁴ Magirius, J.E.F.⁵ Linden, A.⁶

18
- 0141989670
- B. Iliev, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 3215.
- (2003) Helv. Chim. Acta , vol.86 , pp. 3215
- Iliev, B.¹ Linden, A.² Heimgartner, H.³

19
- 29744451807
- B. Iliev, A. Linden, R. W. Kunz, H. Heimgartner, Tetrahedron 2006, 62, 1079.
- (2006) Tetrahedron , vol.62 , pp. 1079
- Iliev, B.¹ Linden, A.² Kunz, R.W.³ Heimgartner, H.⁴

20
- 33646230128
- Ph.D. Thesis, Universität Zürich
- B. Iliev, Ph.D. Thesis, Universität Zürich, 2005.
- (2005)
- Iliev, B.¹

21
- 0346528926
- N. S. Wulfson, V. A. Puchkov, V. N. Bochkarev, B. V. Rozinov, A. M. Zayakoon, M. M. Shemyakin, Y. A. Ovchinnikov, V. T. Ivanov, A. A. Kiryushkin, E. I. Vinigradova, M. Y. Feigina, N. A. Aldanova, Tetrahedron Lett. 1964, 5, 951.
- (1964) Tetrahedron Lett. , vol.5 , pp. 951
- Wulfson, N.S.¹ Puchkov, V.A.² Bochkarev, V.N.³ Rozinov, B.V.⁴ Zayakoon, A.M.⁵ Shemyakin, M.M.⁶ Ovchinnikov, Y.A.⁷ Ivanov, V.T.⁸ Kiryushkin, A.A.⁹ Vinigradova, E.I.¹⁰ Feigina, M.Y.¹¹ Aldanova, N.A.¹²

22
- 33646244334
- N. S. Wulfson, V. A. Puchkov, B. V. Rozinov, A. M. Zayakoon, M. M. Shemyakin, Y. A. Ovchinnikov, A. A. Kiryushkin, V. T. Ivanov, Tetrahedron Lett. 1965, 6, 2793.
- (1965) Tetrahedron Lett. , vol.6 , pp. 2793
- Wulfson, N.S.¹ Puchkov, V.A.² Rozinov, B.V.³ Zayakoon, A.M.⁴ Shemyakin, M.M.⁵ Ovchinnikov, Y.A.⁶ Kiryushkin, A.A.⁷ Ivanov, V.T.⁸

23
- 84981758158
- K. Brockmann, G. Schmidt-Kastner, Chem. Ber. 1955, 88, 57.
- (1955) Chem. Ber. , vol.88 , pp. 57
- Brockmann, K.¹ Schmidt-Kastner, G.²

24
- 0002086994
- M. M. Shemyakin, N. A. Aldanova, R. I. Vinogradova, V. Y. Feigina, Tetrahedron Lett. 1963, 4, 1921.
- (1963) Tetrahedron Lett. , vol.4 , pp. 1921
- Shemyakin, M.M.¹ Aldanova, N.A.² Vinogradova, R.I.³ Feigina, V.Y.⁴

25
- 0014151905
- B. C. Pressman, E. J. Harris, W. S. Jagger, J. N. Johnson, Proc. Natl. Acad. Sci. U.S.A. 1967, 58, 1949.
- (1967) Proc. Natl. Acad. Sci. U.S.A. , vol.58 , pp. 1949
- Pressman, B.C.¹ Harris, E.J.² Jagger, W.S.³ Johnson, J.N.⁴

26
- 0016352907
- Y. A. Ovchinnikov, V. T. Ivanov, A. V. Evstratov, I. I. Mikhaleva, V. F. Bystrov, S. L. Portnova, T. A. Balashova, E. N. Meshcheryakova, V. M. Tul'chinskii, Int. J. Pept. Protein Res. 1974, 6, 465.
- (1974) Int. J. Pept. Protein Res. , vol.6 , pp. 465
- Ovchinnikov, Y.A.¹ Ivanov, V.T.² Evstratov, A.V.³ Mikhaleva, I.I.⁴ Bystrov, V.F.⁵ Portnova, S.L.⁶ Balashova, T.A.⁷ Meshcheryakova, E.N.⁸ Tul'Chinskii, V.M.⁹

27
- 0017102422
- B. C. Pressman, Ann. Rev. Biochem. 1976, 45, 501.
- (1976) Ann. Rev. Biochem. , vol.45 , pp. 501
- Pressman, B.C.¹

28
- 33646267269
- Ph.D. Thesis, Universität Zürich
- J. E. F. Magirius, Ph.D. Thesis, Universität Zürich, 1995.
- (1995)
- Magirius, J.E.F.¹

29
- 0026021427
- H. Heimgartner, Angew. Chem., Int. Ed. 1991, 30, 238.
- (1991) Angew. Chem., Int. Ed. , vol.30 , pp. 238
- Heimgartner, H.¹

30
- 0025319387
- P. Wipf, H. Heimgartner, Helv. Chim. Acta 1990, 73, 13.
- (1990) Helv. Chim. Acta , vol.73 , pp. 13
- Wipf, P.¹ Heimgartner, H.²

31
- 33646260755
- Ph.D. Thesis, Universität Zürich
- W. Altherr, Ph.D. Thesis, Universität Zürich, 1994.
- (1994)
- Altherr, W.¹

32
- 0029875062
- R. Luykx, C. B. Bucher, A. Linden, H. Heimgartner, Helv. Chim. Acta 1996, 79, 527.
- (1996) Helv. Chim. Acta , vol.79 , pp. 527
- Luykx, R.¹ Bucher, C.B.² Linden, A.³ Heimgartner, H.⁴

33
- 0347717887
- R. T. N. Luykx, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 4093.
- (2003) Helv. Chim. Acta , vol.86 , pp. 4093
- Luykx, R.T.N.¹ Linden, A.² Heimgartner, H.³

34
- 0345601955
- N. Pradeille, H. Heimgartner, J. Peptide Sci. 2003, 9, 827.
- (2003) J. Peptide Sci. , vol.9 , pp. 827
- Pradeille, N.¹ Heimgartner, H.²

35
- 26044453600
- N. Pradeille, O. Zerbe, K. Möhle, A. Linden, H. Heimgartner, Chem. Biodiv. 2005, 2, 1127.
- (2005) Chem. Biodiv. , vol.2 , pp. 1127
- Pradeille, N.¹ Zerbe, O.² Möhle, K.³ Linden, A.⁴ Heimgartner, H.⁵

36
- 0032560783
- J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1998, 54, 8721.
- (1998) Tetrahedron , vol.54 , pp. 8721
- Lehmann, J.¹ Linden, A.² Heimgartner, H.³

37
- 0033597275
- J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1999, 55, 5359.
- (1999) Tetrahedron , vol.55 , pp. 5359
- Lehmann, J.¹ Linden, A.² Heimgartner, H.³

38
- 0033064044
- J. Lehmann, A. Linden, H. Heimgartner, Helv. Chim. Acta 1999, 82, 888.
- (1999) Helv. Chim. Acta , vol.82 , pp. 888
- Lehmann, J.¹ Linden, A.² Heimgartner, H.³

39
- 0032701312
- J. Lehmann, A. Linden, H. Heimgartner, Helv. Chim. Acta 1999, 82, 1899.
- (1999) Helv. Chim. Acta , vol.82 , pp. 1899
- Lehmann, J.¹ Linden, A.² Heimgartner, H.³

40
- 33646268481
- Ph.D. Thesis, Universität Zürich
- F. S. Arnhold, Ph.D. Thesis, Universität Zürich, 1997.
- (1997)
- Arnhold, F.S.¹

41
- 12944307840
- T. Jeremic, A. Linden, K. Moehle, H. Heimgartner, Tetrahedron 2005, 61, 1871.
- (2005) Tetrahedron , vol.61 , pp. 1871
- Jeremic, T.¹ Linden, A.² Moehle, K.³ Heimgartner, H.⁴

42
- 11244318259
- T. Jeremic, A. Linden, H. Heimgartner, Helv. Chim. Acta 2004, 87, 3056.
- (2004) Helv. Chim. Acta , vol.87 , pp. 3056
- Jeremic, T.¹ Linden, A.² Heimgartner, H.³

43
- 11244282839
- T. Jeremic, A. Linden, H. Heimgartner, Chem. Biodiv. 2004, 1, 1730.
- (2004) Chem. Biodiv. , vol.1 , pp. 1730
- Jeremic, T.¹ Linden, A.² Heimgartner, H.³

44
- 23044508416
- I. Philipova, A. Linden, H. Heimgartner, Helv. Chim. Acta 2005, 88, 1711.
- (2005) Helv. Chim. Acta , vol.88 , pp. 1711
- Philipova, I.¹ Linden, A.² Heimgartner, H.³

45
- 33646249228
- in preparation
- P. Köttgen, A. Linden, H. Heimgartner, in preparation.
- Köttgen, P.¹ Linden, A.² Heimgartner, H.³

46
- 33646253509
- Ph.D. Thesis, Universität Zürich
- P. Köttgen, Ph.D. Thesis, Universität Zürich, 2006.
- (2006)
- Köttgen, P.¹

47
- 33646252322
- ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee
- C. K. Johnson, ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
- (1976)
- Johnson, C.K.¹

48
- 33748502022
- J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem., Int. Ed. 1995, 34, 1555.
- (1995) Angew. Chem., Int. Ed. , vol.34 , pp. 1555
- Bernstein, J.¹ Davis, R.E.² Shimoni, L.³ Chang, N.-L.⁴

49
- 0001191854
- K. C. Nicolaou, Tetrahedron 1977, 33, 683.
- (1977) Tetrahedron , vol.33 , pp. 683
- Nicolaou, K.C.¹

50
- 0037414319
- Y. Yamashita, S. Saito, H. Ishitani, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3793.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 3793
- Yamashita, Y.¹ Saito, S.² Ishitani, H.³ Kobayashi, S.⁴

51
- 33646269113
- J. J. Wen, C. M. Crews, Tetrahedron Lett. 1998, 39, 77.
- (1998) Tetrahedron Lett. , vol.39 , pp. 77
- Wen, J.J.¹ Crews, C.M.²

52
- 18744398292
- KappaCCD Collect Software
- Delft
- R. Hooft, 'KappaCCD Collect Software', Nonius BV, Delft, 1999.
- (1999) Nonius BV
- Hooft, R.¹

53
- 0031059866
- Macromolecular Crystallography, Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, New York
- Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, New York, 1997, p. 307.
- (1997) 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A , vol.276 , pp. 307
- Otwinowski, Z.¹ Minor, W.²

54
- 0000604488
- SIR92
- A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, 'SIR92', J. Appl. Crystallogr. 1994, 27, 435.
- (1994) J. Appl. Crystallogr. , vol.27 , pp. 435
- Altomare, A.¹ Cascarano, G.² Giacovazzo, C.³ Guagliardi, A.⁴ Burla, M.C.⁵ Polidori, G.⁶ Camalli, M.⁷

55
- 33646234307
- PLATON, Program for the Analysis of Molecular Geometry, University of Utrecht
- A. L. Spek, PLATON, Program for the Analysis of Molecular Geometry, University of Utrecht, 2003.
- (2003)
- Spek, A.L.¹

56
- 0000193015
- Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, Table 6.1.1.1
- a) E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 6.1.1.1, p. 477;
- (1992) International Tables for Crystallography , vol.C , pp. 477
- Maslen, E.N.¹ Fox, A.G.² O'Keefe, M.A.³

57
- 0000029575
- Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, Table 4.2.6.8
- b) D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 4.2.6.8, p. 219;
- (1992) International Tables for Crystallography , vol.C , pp. 219
- Creagh, D.C.¹ McAuley, W.J.²

58
- 0000191360
- Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, Table 4.2.4.3
- c) D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 4.2.4.3, p. 200.
- (1992) International Tables for Crystallography , vol.C , pp. 200
- Creagh, D.C.¹ Hubbell, J.H.²

59
- 19944425329
- R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
- (1965) J. Chem. Phys. , vol.42 , pp. 3175
- Stewart, R.F.¹ Davidson, E.R.² Simpson, W.T.³

60
- 0000940732
- J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
- (1964) Acta Crystallogr. , vol.17 , pp. 781
- Ibers, J.A.¹ Hamilton, W.C.²

61
- 0004150157
- Program for the Refinement of Crystal Structures, University of Göttingen
- G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttingen, 1997.
- (1997) SHELXL97
- Sheldrick, G.M.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.