Angewandte
Chemie
Komarova, M. A. Nowak, B. H. Hahn, P. D. Kwong, G. M. Shaw,
Nature 2003, 422, 307 – 312.
[32] Z.-G. Wang, X. Zhang, M. Visser, D. Live, A. Zatorski, U.
Iserloh, K. O. Lloyd, S. J. Danishefsky, Angew. Chem. 2001, 113,
1778 – 1782; Angew. Chem. Int. Ed. 2001, 40, 1728 – 1732.
[33] Z.-G. Wang, X. Zhang, D. Live, S. J. Danishefsky, Angew. Chem.
2000, 112, 3798 – 3802; Angew. Chem. Int. Ed. 2000, 39, 3652 –
3656.
[34] Since we had conducted the NCL earlier and subsequently in the
complex systems, we are unable to explain the breakdown in the
case at hand. Clearly more work is necessary to define the scope
and limitation of NCL in highly complex settings. Conceivably
we are operating in peptide sequence with 27 and 28 which are
particularly resistant to the methodology which has been
developed. It also possible that the particular glycol-domain
assembled in this case serves to shield the proposed site of
ligation. These issues are being evaluated to allow a more
definitive statement as to scope and limitation of NCL in these
settings.
[35] P. Lloyd-Williams, F. Albericio, E. Giralt, Chemical Approaches
to the Synthesis of Peptides and Proteins, CRC Press, Florida,
1997.
[36] R. R. Flavell, M. Huse, M. Goger, M. Trester-Zedlitz, J. Kuriyan,
T. W. Muir, Org. Lett. 2002, 4, 165 – 168.
[37] Z. Xia, C. D. Smith, J. Org. Chem. 2001, 66, 5241 – 5244.
[38] L. Jiang, K. Burgess, Tetrahedron 2002, 58, 8743 – 8750.
[39] D. Macmillan, A. M. Daines, M. Bayrhuber, S. L. Flitsch, Org.
Lett. 2002, 4, 1467 – 1470.
[40] F. Eisele, J. Kuhlmann, H. Waldmann, Angew. Chem. 2001, 113,
382 – 386; Angew. Chem. Int. Ed. 2001, 40, 369 – 373.
[41] A. Abraham, F. A. Bencsath, A. Shartava, D. G. Kakhniashvili,
S. R. Goodman, Biochemistry 2002, 41, 292 – 296.
[5] P. D. Kwong, M. L. Doyle, D. J. Casper, C. Cicala, S. A. Leavitt,
S. Majeed, T. D. Steenbeke, M. Venturi, I. Chaiken, M. Fung, H.
Katinger, P. W. Parren, J. Robinson, D. Van Ryk, L. Wang, D. R.
Burton, E. Freire, R. Wyatt, J. Sodroski, W. A. Hendrickson, J.
Arthos, Nature 2002, 420, 678 – 682.
[6] H. Geyer, C. Holschbach, G. Hunsmann, J. Schneider, J. Biol.
Chem. 1988, 263, 11760 – 11767.
[7] H. Feinberg, D. A. Mitchell, K. Drickamer, W. I. Weis, Science
2001, 294, 2163 – 2166.
[8] C. A. Bewley, S. Otero-Quintero, J. Am. Chem. Soc. 2001, 123,
3892 – 3902.
[9] A. Trkola, M. Purtscher, T. Muster, C. Ballaun, A. Buchacher, N.
Sullivan, K. Srinivasan, J. Sodroski, J. P. Moore, H. Katinger, J.
Virol. 1996, 70, 1100 – 1108.
[10] G. Stiegler, C. Armbruster, B. Vcelar, H. Stoiber, R. Kunert,
N. L. Michael, L. L. Jagodzinski, C. Ammann, W. Jager, J.
Jacobson, N. Vetter, H. Katinger, AIDS 2002, 16, 2019 – 2025.
[11] C. N. Scanlan, R. Pantophlet, M. R. Wormald, E. Ollmann
Saphire, R. Stanfield, I. A. Wilson, H. Katinger, R. A. Dwek,
P. M. Rudd, D. R. Burton, J. Virol. 2002, 76, 7306 – 7321.
[12] R. W. Sanders, M. Venturi, L. Schiffner, R. Kalyanaraman, H.
Katinger, K. O. Lloyd, P. D. Kwong, J. P. Moore, J. Virol. 2002,
76, 7293 – 7305.
[13] S. R. Hamilton, P. Bobrowicz, B. Bobrowicz, R. C. Davidson, H.
Li, T. Mitchell, J. H. Nett, S. Rausch, T. A. Stadheim, H.
Wischnewski, S. Wildt, T. U. Gerngross, Science 2003, 301,
1244 – 1246.
[14] C. R. Bertozzi, L. L. Kiessling, Science 2001, 291, 2357 – 2364.
[15] H. Herzner, T. Reipen, M. Schultz, H. Kunz, Chem. Rev. 2000,
100, 4495 – 4537.
[16] H. Weiss, C. Unverzagt, Angew. Chem. 2003, 115, 4389 – 4392;
Angew. Chem. Int. Ed. 2003, 42, 4261 – 4263.
[42] G. S. Gendeh, L. C. Young, C. L. de Medeiros, K. Jeyaseelan,
A. L. Harvey, M. C. Chung, Biochemistry 1997, 36, 11461 –
11471.
[43] A. Tiwari, L. J. Hayward, J. Biol. Chem. 2003, 278, 5984 – 5992.
[44] ESMS (m/z): calcd for C154H261N36O70S2 [M+3H+]: 1266.2, found
1266.3; calcd for C154H262N36O70S2 [M+4H+]: 949.9, found: 949.9
[45] In the following paper in this issue, we describe our efforts for
the synthesis of high-mannose-type HIV gp120 glycopeptides
fragments: X. Geng, V. Y. Dudkin, M. Mandal, S. J. Danishefsky,
Angew. Chem. 2004, 116, 2616 – 2619; Angew. Chem. Int. Ed.
2004, 43, 2562 – 2565.
[17] P. H. Seeberger, M. T. Bilodeau, S. J. Danishefsky, Aldrichimica
Acta 1997, 30, 75 – 92.
[18] S. J. Danishefsky, M. T. Bilodeau, Angew. Chem. 1996, 108,
1482 – 1522; Angew. Chem. Int. Ed. Engl. 1996, 35, 1380 – 1419.
[19] D. Crich, S. X. Sun, Tetrahedron 1998, 54, 8321 – 8348.
[20] V. Y. Dudkin, D. Crich, Tetrahedron Lett. 2003, 44, 1787 – 1789.
[21] L. M. Likhosherstov, O. S. Novikova, V. A. Derevitskaja, N. K.
Kochetkov, Carbohydr. Res. 1986, 146, C1-C5.
[22] S. T. Cohen-Anisfeld, P. T. Lansbury, J. Am. Chem. Soc. 1993,
115, 10531 – 10537.
[23] P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. H. Kent, Science
1994, 266, 776 – 779.
[24] a) L. A. Carpino, J. Am. Chem. Soc. 1993, 115,4397 – 4398; b) U.
Sprengard, M. Schudok, W. Schmidt, G. Kretzschmar, H. Kunz,
Angew. Chem. 1996, 108, 359 – 362; Angew. Chem. Int. Ed. Engl.
1996, 35, 321 – 324; c) J. S. Miller, V. Y. Dudkin, G. J. Lyon, T. W.
Muir, S. J. Danishefsky, Angew. Chem. 2003, 115, 447 – 450;
Angew. Chem. Int. Ed. 2003, 42, 431 – 434.
[25] V. Y. Dudkin, J. S. Miller, S. J. Danishefsky, J. Am. Chem. Soc.
2004, 126, 736 – 738.
[26] T. J. Tolbert, C. H. Wong, J. Am. Chem. Soc. 2000, 122, 5421 –
5428.
[27] V. Y. Dudkin, J. S. Miller, S. J. Danishefsky, Tetrahedron Lett.
2003, 44, 1791 – 1793. The stereochemistry of glycosidic linkages
1
in 7 was confirmed by a combination of HMQC and JCH
measurements; for details, see Supporting Information.
[28] Y. M. Zhang, J. M. Mallet, P. Sinay¨, Carbohydr. Res. 1992, 236,
73 – 88.
[29] L. Jiang, T. H. Chan, Tetrahedron Lett. 1998, 39, 355 – 358.
[30] A. Vasella, C. Witzig, J. L. Chiara, M. Martin-Lomas, Helv.
Chim. Acta 1991, 74, 2073 – 2077.
[31] U. Iserloh, V. Dudkin, Z.-G. Wang, S. J. Danishefsky, Tetrahe-
dron Lett. 2002, 43, 7027 – 7030.
Angew. Chem. Int. Ed. 2004, 43, 2557 –2561
ꢀ 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
2561