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1
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0010460437
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San Francisco, CA ORGN 579
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Presented at the 213th National ACS Meeting, San Francisco, CA 1997 ORGN 579.
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(1997)
213th National ACS Meeting
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2
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0028243847
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The first synthesis of amide-linked sugars from SAA was reported by Fuchs and Lehmann
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The first synthesis of amide-linked sugars from SAA was reported by Fuchs and Lehmann.
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25
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(b) Liang, R.; Yan, L.; Loebach, J.; Ge, M.; Yozumi, Y.; Sekanina, K.; Horan, N.; Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W. C.; Kahne, D. Science 1996, 274, 1520.
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26
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1542711751
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July 2-7, Absract A74-75
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A plethora of terms have been proposed in the literature for compounds derived from SAA. These include carbopeptoids, saccharidepeptide hybrids, glycosamino acids, peptidosaccharides, saccharopeptides, and amide-linked carbohydrates, to name a few. In some cases, the SAA are linked to each other to give compounds that are completely carbohydrate-based. In other cases, they are linked to naturally occurring amino acids. In order to readily distinguish between the two possibilities, we refer to the former class as amide-linked sugars and the latter class as saccharopeptides. The term saccharopeptide itself was, to our knowledge, first proposed by Fugedi to describe compounds that we now refer to as amide-linked sugars. See Fugedi, P.; Peto, Cs; Wlasichuk, K. 8th European Carbohydrate Symposium, July 2-7, 1995, Absract A74-75.
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(1995)
8th European Carbohydrate Symposium
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Fugedi, P.1
Peto, Cs.2
Wlasichuk, K.3
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27
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0031048319
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For lead references see (a) Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, W. G.; Stevens, R. C. J. Am. Chem Soc. 1997, 119, 681. (b) Sabesan, S.; Neira, S.; Davidson, F.; Duus, J. O.; Bock, K. J. Am. Chem. Soc. 1995, 116, 1616. (c) von Itzstein, M.; Wu, W.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryn, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M. and Penn, C. R. Nature (London) 1993, 363, 418.
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Tai, C.Y.10
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Stevens, R.C.12
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0028147159
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For lead references see (a) Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, W. G.; Stevens, R. C. J. Am. Chem Soc. 1997, 119, 681. (b) Sabesan, S.; Neira, S.; Davidson, F.; Duus, J. O.; Bock, K. J. Am. Chem. Soc. 1995, 116, 1616. (c) von Itzstein, M.; Wu, W.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryn, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M. and Penn, C. R. Nature (London) 1993, 363, 418.
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Bock, K.5
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For lead references see (a) Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, W. G.; Stevens, R. C. J. Am. Chem Soc. 1997, 119, 681. (b) Sabesan, S.; Neira, S.; Davidson, F.; Duus, J. O.; Bock, K. J. Am. Chem. Soc. 1995, 116, 1616. (c) von Itzstein, M.; Wu, W.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryn, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M. and Penn, C. R. Nature (London) 1993, 363, 418.
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Smythe, M.L.8
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Oliver, S.W.10
Colman, P.M.11
Varghese, J.N.12
Ryn, D.M.13
Woods, J.M.14
Bethell, R.C.15
Hotham, V.J.16
Cameron, J.M.17
Penn, C.R.18
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33
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Leaving out HOBT does not affect the yield of the reaction. It was used to suppress racemization
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Leaving out HOBT does not affect the yield of the reaction. It was used to suppress racemization.
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34
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We are currently studying the problems associated with coupling reactions involving 10
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We are currently studying the problems associated with coupling reactions involving 10.
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(a) Tailler, D.; Jacquinet, J.-C.; Noirot, A.-M.; Beau, J.-M. J. Chem. Soc., Perkin Trans. 1 1992, 3163.
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and references therein
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Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palacios, J. C.; Valencia, C. Tetrahedron Lett. 1993, 34, 1359 and references therein.
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39
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1542397164
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Full experimental details of this work and the biological testing of this and other compounds will be reported in a forthcoming publication from our laboratory
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Full experimental details of this work and the biological testing of this and other compounds will be reported in a forthcoming publication from our laboratory.
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1542501983
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submitted for publication
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Szabo L.; Smith, B. L.; McReynolds, K. D.; Parrill, A. L.; Morris, E. R.; Gervay, J. J. Org. Chem., submitted for publication.
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