-
1
-
-
67849092526
-
-
See preceding two papers: a
-
See preceding two papers: (a) Tan, Z.; Shang, S.; Halkina, T.; Yuan, Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2009, 131, 5424-5431.
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 5424-5431
-
-
Tan, Z.1
Shang, S.2
Halkina, T.3
Yuan, Y.4
Danishefsky, S.J.5
-
2
-
-
67849101900
-
-
(b) Yuan, Y.; Chen, J.; Wan, Q.; Tan, Z.; Chen, G.; Kan, C.; Danishefsky, S. J. J. Am. Chem. Soc. 2009, 131, 5432-5437.
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 5432-5437
-
-
Yuan, Y.1
Chen, J.2
Wan, Q.3
Tan, Z.4
Chen, G.5
Kan, C.6
Danishefsky, S.J.7
-
3
-
-
0035805278
-
-
(a) Wang, Z.-G.; Zhang, X.; Visser, M.; Live, D.; Zatorski, A.; Iserloh, U.; Lloyd, K. O.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1728-1732.
-
(2001)
Angew. Chem., Int. Ed
, vol.40
, pp. 1728-1732
-
-
Wang, Z.-G.1
Zhang, X.2
Visser, M.3
Live, D.4
Zatorski, A.5
Iserloh, U.6
Lloyd, K.O.7
Danishefsky, S.J.8
-
4
-
-
0037468055
-
-
(b) Miller, J. S.; Dudkin, V. Y.; Lyon, G. J.; Muir, T. W.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 431-434.
-
(2003)
Angew. Chem., Int. Ed
, vol.42
, pp. 431-434
-
-
Miller, J.S.1
Dudkin, V.Y.2
Lyon, G.J.3
Muir, T.W.4
Danishefsky, S.J.5
-
5
-
-
33745263964
-
-
(c) Wu, B.; Chen, J.; Warren, J. D.; Chen, G.; Hua, Z.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2006, 45, 4116-4125.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 4116-4125
-
-
Wu, B.1
Chen, J.2
Warren, J.D.3
Chen, G.4
Hua, Z.5
Danishefsky, S.J.6
-
6
-
-
33749520608
-
-
(d) Wu, B.; Tan, Z.; Chen, G.; Chen, J.; Hua, Z.; Wan, Q.; Ranganathan, K.; Danishefsky, S. J. Tetrahedron Lett. 2006, 47, 8009-8011.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 8009-8011
-
-
Wu, B.1
Tan, Z.2
Chen, G.3
Chen, J.4
Hua, Z.5
Wan, Q.6
Ranganathan, K.7
Danishefsky, S.J.8
-
7
-
-
33749507176
-
-
(e) Chen, J.; Chen, G.; Wu, B.; Wan, Q.; Tan, Z.; Hua, Z.; Danishefsky, S. J. Tetrahedron Lett 2006, 47, 8013-8016.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 8013-8016
-
-
Chen, J.1
Chen, G.2
Wu, B.3
Wan, Q.4
Tan, Z.5
Hua, Z.6
Danishefsky, S.J.7
-
8
-
-
35048868425
-
-
(f) Chen, G.; Wan, Q.; Tan, Z.; Kan, C.; Hua, Z.; Ranganathan, K.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2007, 46, 7383-7387.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 7383-7387
-
-
Chen, G.1
Wan, Q.2
Tan, Z.3
Kan, C.4
Hua, Z.5
Ranganathan, K.6
Danishefsky, S.J.7
-
9
-
-
37349094422
-
-
(g) Wan, Q.; Danishefsky, S. J. Angew, Chem., Int. Ed. 2007, 46, 9248-9252.
-
(2007)
Angew, Chem., Int. Ed
, vol.46
, pp. 9248-9252
-
-
Wan, Q.1
Danishefsky, S.J.2
-
10
-
-
56749092136
-
-
(h) Wan, Q.; Chen, J.; Yuan, Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2008, 130, 15814-15816.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 15814-15816
-
-
Wan, Q.1
Chen, J.2
Yuan, Y.3
Danishefsky, S.J.4
-
11
-
-
2542548800
-
-
(i) Warren, J. D.; Miller, J. S.; Keding, S. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 6576-6578.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 6576-6578
-
-
Warren, J.D.1
Miller, J.S.2
Keding, S.J.3
Danishefsky, S.J.4
-
13
-
-
67849092356
-
-
For general reviews on EPO, see: a, Wiley-VCH Verlag GmbH and Co. KGaA: Weinheim
-
For general reviews on EPO, see: (a) Sytkowski, A. J. Erythropoietin; Wiley-VCH Verlag GmbH and Co. KGaA: Weinheim, 2004.
-
(2004)
Erythropoietin
-
-
Sytkowski, A.J.1
-
15
-
-
0026702568
-
-
Higuchi, M.; Masayoshi, O.; Kuboniwa, H.; Tomonoh, K.; Shimonaka, Y.; Ochi, N. J. Biol. Chem. 1992, 267, 7703-7709.
-
(1992)
J. Biol. Chem
, vol.267
, pp. 7703-7709
-
-
Higuchi, M.1
Masayoshi, O.2
Kuboniwa, H.3
Tomonoh, K.4
Shimonaka, Y.5
Ochi, N.6
-
16
-
-
0000212930
-
-
(a) Egrie, J. C.; Grant, J. R.; Gillies, D. K.; Aoki, K. H.; Strickland, T. W. Glycoconjugate J. 1993, 10, 263.
-
(1993)
Glycoconjugate J
, vol.10
, pp. 263
-
-
Egrie, J.C.1
Grant, J.R.2
Gillies, D.K.3
Aoki, K.H.4
Strickland, T.W.5
-
20
-
-
0036462601
-
-
(b) Roth, J. Chem Rev. 2002, 102, 285-303.
-
(2002)
Chem Rev
, vol.102
, pp. 285-303
-
-
Roth, J.1
-
22
-
-
0027944205
-
-
Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
-
(1994)
Science
, vol.266
, pp. 776-779
-
-
Dawson, P.E.1
Muir, T.W.2
Clark-Lewis, I.3
Kent, S.B.H.4
-
23
-
-
0033596308
-
-
For the first example of glycoprotein chemical synthesis using NCL, see: a
-
For the first example of glycoprotein chemical synthesis using NCL, see: (a) Shin, Y.; Winans, K. A.; Backes, B. J.; Kent, S. B. H.; Ellman, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 1999, 121, 11684-11689.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 11684-11689
-
-
Shin, Y.1
Winans, K.A.2
Backes, B.J.3
Kent, S.B.H.4
Ellman, J.A.5
Bertozzi, C.R.6
-
24
-
-
34248230589
-
-
For recent examples of protein synthesis using NCL, see: b
-
For recent examples of protein synthesis using NCL, see: (b) Torbeev, V. Y.; Kent, S. B. H. Angew. Chem., Int. Ed. 2007, 46, 1667-1670.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 1667-1670
-
-
Torbeev, V.Y.1
Kent, S.B.H.2
-
25
-
-
34247569910
-
-
(c) Durek, T.; Torbeev, V. Y.; Kent, S. B. H. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 4846-4851.
-
(2007)
Proc. Natl. Acad. Sci. U.S.A
, vol.104
, pp. 4846-4851
-
-
Durek, T.1
Torbeev, V.Y.2
Kent, S.B.H.3
-
26
-
-
0033791223
-
-
For a review on NCL, see: d
-
For a review on NCL, see: (d) Dawson, P. E.; Kent, S. B. H. Annu. Rev. Biochem. 2000, 69, 923-960.
-
(2000)
Annu. Rev. Biochem
, vol.69
, pp. 923-960
-
-
Dawson, P.E.1
Kent, S.B.H.2
-
27
-
-
40149092211
-
-
Note that the sialyloligosaccharide was isolated from hen's egg yolk and does not contain any fucose unit. See
-
Note that the sialyloligosaccharide was isolated from hen's egg yolk and does not contain any fucose unit. See: Yamamoto, N.; Tanabe, Y.; Okamoto, R.; Dawson, P. E.; Kajihara, Y. J. Am. Chem. Soc. 2008, 130, 501-510.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 501-510
-
-
Yamamoto, N.1
Tanabe, Y.2
Okamoto, R.3
Dawson, P.E.4
Kajihara, Y.5
-
28
-
-
0019529504
-
-
For other direct condensation methods, see: a
-
For other direct condensation methods, see: (a) Blake, J. Int. J. Pept. Protein Res. 1981, 17, 273-274.
-
(1981)
Int. J. Pept. Protein Res
, vol.17
, pp. 273-274
-
-
Blake, J.1
-
29
-
-
0024500435
-
-
(b) Aimoto, S.; Mizoguchi, N.; Hojo, H.; Yoshimura, S. Bull. Chem. Soc. Jpn. 1989, 62, 524-531.
-
(1989)
Bull. Chem. Soc. Jpn
, vol.62
, pp. 524-531
-
-
Aimoto, S.1
Mizoguchi, N.2
Hojo, H.3
Yoshimura, S.4
-
30
-
-
0033397158
-
-
(c) Aimoto, S. Biopolymers 1999, 51, 247-265.
-
(1999)
Biopolymers
, vol.51
, pp. 247-265
-
-
Aimoto, S.1
-
31
-
-
46749125397
-
-
(d) Payne, R. J.; Ficht, S.; Greenberg, W. A.; Wong, C.-H. Angew. Chem., Int. Ed. 2008, 47, 4411-4415.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 4411-4415
-
-
Payne, R.J.1
Ficht, S.2
Greenberg, W.A.3
Wong, C.-H.4
-
32
-
-
49149087660
-
-
Okamoto, R.; Kajihara, Y. Angew. Chem., Int. Ed. 2008, 47, 5402-5406.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 5402-5406
-
-
Okamoto, R.1
Kajihara, Y.2
-
33
-
-
0030037155
-
-
For other examples of auxiliary-based cysteine-free ligations, see: a
-
For other examples of auxiliary-based cysteine-free ligations, see: (a) Canne, L. E.; Bark, S. J.; Kent, S. B. H. J. Am. Chem. Soc. 1996, 118, 5891-5896.
-
(1996)
J. Am. Chem. Soc
, vol.118
, pp. 5891-5896
-
-
Canne, L.E.1
Bark, S.J.2
Kent, S.B.H.3
-
34
-
-
0035804493
-
-
(b) Botti, P.; Carrasco, M. R.; Kent, S. B. H. Tetrahedron Lett. 2001, 42, 1831-1833.
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 1831-1833
-
-
Botti, P.1
Carrasco, M.R.2
Kent, S.B.H.3
-
35
-
-
0034824640
-
-
(c) Marinzi, C.; Bark, S. J.; Offer, J.; Dawson, P. E. Bioorg. Med. Chem. 2001, 9, 2323-2328.
-
(2001)
Bioorg. Med. Chem
, vol.9
, pp. 2323-2328
-
-
Marinzi, C.1
Bark, S.J.2
Offer, J.3
Dawson, P.E.4
-
36
-
-
0035811061
-
-
(d) Low, D. W.; Hill, M. G.; Carrasco, M. R.; Kent, S. B. H.; Botti, P. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 6554-6559.
-
(2001)
Proc. Natl. Acad. Sci. U.S.A
, vol.98
, pp. 6554-6559
-
-
Low, D.W.1
Hill, M.G.2
Carrasco, M.R.3
Kent, S.B.H.4
Botti, P.5
-
37
-
-
0036570182
-
-
(e) Offer, J.; Boddy, C. N. C.; Dawson, P. E. J. Am. Chem. Soc. 2002, 124, 4642- 4646.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 4642-4646
-
-
Offer, J.1
Boddy, C.N.C.2
Dawson, P.E.3
-
39
-
-
35948946622
-
-
and references therein
-
(g) Payne, R. J.; Ficht, S.; Tang, S.; Brik, A.; Yang, Y.-Y.; Case, D. A.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 13527-13536, and references therein.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 13527-13536
-
-
Payne, R.J.1
Ficht, S.2
Tang, S.3
Brik, A.4
Yang, Y.-Y.5
Case, D.A.6
Wong, C.-H.7
-
41
-
-
0035977638
-
-
For other studies on alanine ligations, see: a
-
For other studies on alanine ligations, see: (a) Yan, L. Z.; Dawson, P. E. J. Am. Chem. Soc. 2001, 123, 526-533,
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 526-533
-
-
Yan, L.Z.1
Dawson, P.E.2
-
42
-
-
33847791752
-
-
and references therein. (b) Pentelute, B.; Kent, S. B. H. Org. Lett. 2007, 9, 687-690.
-
and references therein. (b) Pentelute, B.; Kent, S. B. H. Org. Lett. 2007, 9, 687-690.
-
-
-
-
43
-
-
54249149331
-
-
Chen, J.; Wan, Q.; Yuan, Y.; Zhu, J.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2008, 47, 8521-8524.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 8521-8524
-
-
Chen, J.1
Wan, Q.2
Yuan, Y.3
Zhu, J.4
Danishefsky, S.J.5
-
44
-
-
52449084906
-
-
For other studies on valine ligations, see
-
For other studies on valine ligations, see: Haase, C.; Rohde, H.; Seitz, O. Angew. Chem., Int. Ed. 2008, 47, 6807-6810.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 6807-6810
-
-
Haase, C.1
Rohde, H.2
Seitz, O.3
-
46
-
-
67849128630
-
-
For other studies on homocysteine ligations, see
-
For other studies on homocysteine ligations, see: Tam, J. P.; Yu, Q. Biopolymers 1998, 46, 5402-5406.
-
(1998)
Biopolymers
, vol.46
, pp. 5402-5406
-
-
Tam, J.P.1
Yu, Q.2
-
47
-
-
67849111478
-
-
In addition to alanine, valine, and homocysteine ligations, a phenylalanine ligation has also been reported. See: (a) Botti, P, Tchertchian, S. WO 133962, 2006
-
In addition to alanine, valine, and homocysteine ligations, a phenylalanine ligation has also been reported. See: (a) Botti, P.; Tchertchian, S. WO 133962, 2006.
-
-
-
-
49
-
-
67849104564
-
-
Following completion of our studies, C.-H. Wong and co-workers published a direct aminolysis method that could, in theory, be applied to the synthesis of our glycopeptide fragment. See ref 11d
-
Following completion of our studies, C.-H. Wong and co-workers published a direct aminolysis method that could, in theory, be applied to the synthesis of our glycopeptide fragment. See ref 11d.
-
-
-
-
50
-
-
33745267206
-
-
Wu, B.; Hua, Z.; Warren, J. D.; Ranganathan, K.; Wan, Q.; Chen, G.; Tan, Z.; Chen, J.; Endo, A.; Danishefsky, S. J. Tetrahedron Lett. 2006, 47, 5577-5579.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 5577-5579
-
-
Wu, B.1
Hua, Z.2
Warren, J.D.3
Ranganathan, K.4
Wan, Q.5
Chen, G.6
Tan, Z.7
Chen, J.8
Endo, A.9
Danishefsky, S.J.10
-
51
-
-
84869564899
-
-
Mepro)-OH) to avoid unwanted aspartimide formation.
-
Mepro)-OH) to avoid unwanted aspartimide formation.
-
-
-
-
54
-
-
84869578811
-
-
19 has not epimerized, model studies with the corresponding disaccharide substrates indicate formation of a separable mixture of diastereomers in a 4:1 ratio.
-
19 has not epimerized, model studies with the corresponding disaccharide substrates indicate formation of a separable mixture of diastereomers in a 4:1 ratio.
-
-
-
-
56
-
-
67849130488
-
-
Peptide 19 was prepared in two steps from 33, see the Supporting Information for synthesis.
-
Peptide 19 was prepared in two steps from 33, see the Supporting Information for synthesis.
-
-
-
-
57
-
-
33746299267
-
-
Other examples of competitive intramolecular NCL have been observed. See: a
-
Other examples of competitive intramolecular NCL have been observed. See: (a) Bang, D.; Pentelute, B. L.; Kent, S. B. H. Angew. Chem., Int. Ed. 2006, 45, 3985-3988.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 3985-3988
-
-
Bang, D.1
Pentelute, B.L.2
Kent, S.B.H.3
-
58
-
-
34248230589
-
-
(b) Torbeev, V. Y.; Kent, S. B. H. Angew. Chem., Int. Ed. 2007, 46, 1667-1670.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 1667-1670
-
-
Torbeev, V.Y.1
Kent, S.B.H.2
|