SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 53, Issue 45, 2014, Pages 12244-12247

Formation and Rearrangement of Homoserine Depsipeptides and Depsiproteins in the α-Ketoacid-Hydroxylamine Ligation with 5-Oxaproline

(4) Wucherpfennig, Thomas G a Rohrbacher, Florian a Pattabiraman, Vijaya R a Bode, Jeffrey W a,b

a ETH ZURICH (Switzerland)

b NAGOYA UNIVERSITY (Japan)

Author keywords

chemoselectivity; depsipeptides; ligation; proteins; reaction mechanisms

Indexed keywords

AMIDES; ESTERS; PEPTIDES; PROTEINS; SYNTHESIS (CHEMICAL);

CHEMICAL LIGATION; CHEMO-SELECTIVITY; DEPSIPEPTIDE; DEPSIPEPTIDES; LIGATION; POSSIBLE MECHANISMS; PRIMARY PRODUCTS; REACTION MECHANISM;

SURGICAL EQUIPMENT;

5-OXAPROLINE; HYDROXYLAMINE; OLIGOPEPTIDE; PROLINE;

AMINO ACID SEQUENCE; ANALOGS AND DERIVATIVES; CHEMISTRY; MOLECULAR GENETICS;

AMINO ACID SEQUENCE; HYDROXYLAMINES; MOLECULAR SEQUENCE DATA; OLIGOPEPTIDES; PROLINE;

EID: 84907838502 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201406097 Document Type: Article

Times cited : (42)

References (39)

1
- 84887432826
- S. B. H. Kent, Angew. Chem. Int. Ed. 2013, 52, 11988-11996;
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 11988-11996
- Kent, S.B.H.¹

2
- 84953646270
- Angew. Chem. 2013, 125, 12208-12217;
- (2013) Angew. Chem. , vol.125 , pp. 12208-12217

3
- 62449282062
- S. B. H. Kent, Chem. Soc. Rev. 2009, 38, 338-351;
- (2009) Chem. Soc. Rev. , vol.38 , pp. 338-351
- Kent, S.B.H.¹

4
- 51449087558
- R. Kleineweischede, C. P. R. Hackenberger, Angew. Chem. Int. Ed. 2008, 47, 5984-5988;
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5984-5988
- Kleineweischede, R.¹ Hackenberger, C.P.R.²

5
- 57749097621
- Angew. Chem. 2008, 120, 6073-6077;
- (2008) Angew. Chem. , vol.120 , pp. 6073-6077

6
- 84866416513
- L. Raibaut, N. Ollivier, O. Melnyk, Chem. Soc. Rev. 2012, 41, 7001-7015.
- (2012) Chem. Soc. Rev. , vol.41 , pp. 7001-7015
- Raibaut, L.¹ Ollivier, N.² Melnyk, O.³

7
- 84862089672
- V. R. Pattabiraman, A. O. Ogunkoya, J. W. Bode, Angew. Chem. Int. Ed. 2012, 51, 5114-5118;
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 5114-5118
- Pattabiraman, V.R.¹ Ogunkoya, A.O.² Bode, J.W.³

8
- 84865857972
- Angew. Chem. 2012, 124, 5204-5208;
- (2012) Angew. Chem. , vol.124 , pp. 5204-5208

9
- 84866433550
- A. O. Ogunkoya, V. R. Pattabiraman, J. W. Bode, Angew. Chem. Int. Ed. 2012, 51, 9693-9697;
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 9693-9697
- Ogunkoya, A.O.¹ Pattabiraman, V.R.² Bode, J.W.³

10
- 84911485143
- Angew. Chem. 2012, 124, 9831-9835;
- (2012) Angew. Chem. , vol.124 , pp. 9831-9835

11
- 33746190644
- J. W. Bode, R. M. Fox, K. D. Baucom, Angew. Chem. Int. Ed. 2006, 45, 1248-1252;
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1248-1252
- Bode, J.W.¹ Fox, R.M.² Baucom, K.D.³

12
- 33845304667
- Angew. Chem. 2006, 118, 1270-1274.
- (2006) Angew. Chem. , vol.118 , pp. 1270-1274

13
- 0027944205
- P. E. Dawson, T. W. Muir, I. Clarklewis, S. B. H. Kent, Science 1994, 266, 776-779;
- (1994) Science , vol.266 , pp. 776-779
- Dawson, P.E.¹ Muir, T.W.² Clarklewis, I.³ Kent, S.B.H.⁴

14
- 80355130228
- P. E. Dawson, Isr. J. Chem. 2011, 51, 862-867.
- (2011) Isr. J. Chem. , vol.51 , pp. 862-867
- Dawson, P.E.¹

15
- 84958193374
- We chose this particular ligation to illustrate the formation of the ester products as the starting materials for the ligation and both the ester and the amide products are well-resolved by HPLC analysis
- We chose this particular ligation to illustrate the formation of the ester products as the starting materials for the ligation and both the ester and the amide products are well-resolved by HPLC analysis.

16
- 0028223433
- C. F. Liu, J. P. Tam, Proc. Natl. Acad. Sci. USA 1994, 91, 6584-6588.
- (1994) Proc. Natl. Acad. Sci. USA , vol.91 , pp. 6584-6588
- Liu, C.F.¹ Tam, J.P.²

17
- 0742322008
- L. Mouls, G. Subra, C. Enjalbal, J. Martinez, J.-L. Aubagnac, Tetrahedron Lett. 2004, 45, 1173-1178.
- (2004) Tetrahedron Lett. , vol.45 , pp. 1173-1178
- Mouls, L.¹ Subra, G.² Enjalbal, C.³ Martinez, J.⁴ Aubagnac, J.-L.⁵

18
- 84855472327
- I. Pusterla, J. W. Bode, Angew. Chem. Int. Ed. 2012, 51, 513-516;
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 513-516
- Pusterla, I.¹ Bode, J.W.²

19
- 84861593533
- Angew. Chem. 2012, 124, 528-531.
- (2012) Angew. Chem. , vol.124 , pp. 528-531

20
- 33847802171
- D. S. Kemp, K. G. Paul, J. Am. Chem. Soc. 1975, 97, 7305-7312;
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 7305-7312
- Kemp, D.S.¹ Paul, K.G.²

21
- 0000467257
- D. S. Kemp, D. D. Cox, K. G. Paul, J. Am. Chem. Soc. 1975, 97, 7312-7318.
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 7312-7318
- Kemp, D.S.¹ Cox, D.D.² Paul, K.G.³

22
- 0031682989
- G. T. Lee, A. Kucerovy, K. Prasad, O. Repic, T. J. Blacklock, Synth. Commun. 1998, 28, 4009-4018.
- (1998) Synth. Commun. , vol.28 , pp. 4009-4018
- Lee, G.T.¹ Kucerovy, A.² Prasad, K.³ Repic, O.⁴ Blacklock, T.J.⁵

23
- 0033306224
- W. J. Dixon, F. Hibbert, Can. J. Chem. 1999, 77, 1035-1041;
- (1999) Can. J. Chem. , vol.77 , pp. 1035-1041
- Dixon, W.J.¹ Hibbert, F.²

24
- 0347138676
- W. J. Dixon, F. Hibbert, J. F. Mills, Perkin Trans. 2 1997, 1503-1509.
- (1997) Perkin Trans. 2 , pp. 1503-1509
- Dixon, W.J.¹ Hibbert, F.² Mills, J.F.³

25
- 84958193375
- Attempts to trap the putative nitrilium intermediate with nucleophiles other than water in ligations with 5-oxaproline gave only ester and amide products. Attempts to trap the intermediates formed from other hydroxylamines, such as O-Bz-hydroxylamines, were also unsuccessful.
- Attempts to trap the putative nitrilium intermediate with nucleophiles other than water in ligations with 5-oxaproline gave only ester and amide products. Attempts to trap the intermediates formed from other hydroxylamines, such as O-Bz-hydroxylamines, were also unsuccessful.

26
- 79952756911
- T. Narumi, J. W. Bode, Heterocycles 2011, 82, 1515-1525;
- (2011) Heterocycles , vol.82 , pp. 1515-1525
- Narumi, T.¹ Bode, J.W.²

27
- 32244438956
- N. Carrillo, E. A. Davalos, J. A. Russak, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 1452-1453.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1452-1453
- Carrillo, N.¹ Davalos, E.A.² Russak, J.A.³ Bode, J.W.⁴

28
- 34247485404
- references therein
- G. Tuchscherer, A. Chandravarkar, M.-S. Camus, J. Bétard, K. Murat, A. Schmid, R. Mimna, H. A. Lashuel, M. Mutter, Biopolymers 2007, 88, 239-252, and references therein;
- (2007) Biopolymers , vol.88 , pp. 239-252
- Tuchscherer, G.¹ Chandravarkar, A.² Camus, M.-S.³ Bétard, J.⁴ Murat, K.⁵ Schmid, A.⁶ Mimna, R.⁷ Lashuel, H.A.⁸ Mutter, M.⁹

29
- 54749102251
- M. Vila-Perellõ, Y. Hori, M. Ribõ, T. W. Muir, Angew. Chem. Int. Ed. 2008, 47, 7764-7767;
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7764-7767
- Vila-Perellõ, M.¹ Hori, Y.² Ribõ, M.³ Muir, T.W.⁴

30
- 65549159855
- Angew. Chem. 2008, 120, 7878-7881;
- (2008) Angew. Chem. , vol.120 , pp. 7878-7881

31
- 84883237654
- L. Baumann, A. G. Beck-Sickinger, Angew. Chem. Int. Ed. 2013, 52, 9550-9553;
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 9550-9553
- Baumann, L.¹ Beck-Sickinger, A.G.²

32
- 84911464710
- Angew. Chem. 2013, 125, 9729-9732.
- (2013) Angew. Chem. , vol.125 , pp. 9729-9732

33
- 4444382945
- L. A. Carpino, E. Krause, C. D. Sferdean, M. Schümann, H. Fabian, M. Bienert, M. Beyermann, Tetrahedron Lett. 2004, 45, 7519-7523.
- (2004) Tetrahedron Lett. , vol.45 , pp. 7519-7523
- Carpino, L.A.¹ Krause, E.² Sferdean, C.D.³ Schümann, M.⁴ Fabian, H.⁵ Bienert, M.⁶ Beyermann, M.⁷

34
- 1642458245
- Y. Sohma, M. Sasaki, Y. Hayashi, T. Kimura, Y. Kiso, Chem. Commun. 2004, 124-125;
- (2004) Chem. Commun. , pp. 124-125
- Sohma, Y.¹ Sasaki, M.² Hayashi, Y.³ Kimura, T.⁴ Kiso, Y.⁵

35
- 84898074134
- F. Liu, E. Y. Luo, D. B. Flora, A. R. Mezo, Angew. Chem. Int. Ed. 2014, 53, 3983-3987;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 3983-3987
- Liu, F.¹ Luo, E.Y.² Flora, D.B.³ Mezo, A.R.⁴

36
- 84954392236
- Angew. Chem. 2014, 126, 4064-4068.
- (2014) Angew. Chem. , vol.126 , pp. 4064-4068

37
- 77955044829
- Y. Sohma, Q.-X. Hua, J. Whittaker, M. A. Weiss, S. B. H. Kent, Angew. Chem. Int. Ed. 2010, 49, 5489-5493;
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 5489-5493
- Sohma, Y.¹ Hua, Q.-X.² Whittaker, J.³ Weiss, M.A.⁴ Kent, S.B.H.⁵

38
- 78249269362
- Angew. Chem. 2010, 122, 5621-5625;
- (2010) Angew. Chem. , vol.122 , pp. 5621-5625

39
- 84874621257
- M. Avital-Shmilovici, K. Mandal, Z. P. Gates, N. B. Phillips, M. A. Weiss, S. B. H. Kent, J. Am. Chem. Soc. 2013, 135, 3173-3185.
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 3173-3185
- Avital-Shmilovici, M.¹ Mandal, K.² Gates, Z.P.³ Phillips, N.B.⁴ Weiss, M.A.⁵ Kent, S.B.H.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.