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Volumn 62, Issue 22, 1997, Pages 7801-7805

Solution Phase Synthesis of Amide-Linked N-Acetyl Neuraminic Acid, α-Amino Acid, and Sugar Amino Acid Conjugates

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0001231422     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9711246     Document Type: Article
Times cited : (29)

References (41)
  • 1
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    • San Francisco, CA ORGN 579
    • Presented at the 213th National ACS Meeting, San Francisco, CA 1997 ORGN 579.
    • (1997) 213th National ACS Meeting
  • 4
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    • and references cited therein
    • Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650 and references cited therein.
    • (1997) J. Org. Chem. , vol.62 , pp. 3650
    • Rademann, J.1    Schmidt, R.R.2
  • 5
    • 0000688963 scopus 로고
    • To our knowledge the first example of a synthetic SAA was reported by Paulsen in 1955. Heyns, K.; Paulsen, H. Chem. Ber. 1955, 88, 188.
    • (1955) Chem. Ber. , vol.88 , pp. 188
    • Heyns, K.1    Paulsen, H.2
  • 6
    • 1542606716 scopus 로고    scopus 로고
    • The first synthesis of amide-linked sugars from SAA was reported by Fuchs and Lehmann
    • The first synthesis of amide-linked sugars from SAA was reported by Fuchs and Lehmann.
  • 26
    • 1542711751 scopus 로고
    • July 2-7, Absract A74-75
    • 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.
    • (1995) 8th European Carbohydrate Symposium
    • Fugedi, P.1    Peto, Cs.2    Wlasichuk, K.3
  • 29
    • 0031048319 scopus 로고    scopus 로고
    • 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.
    • (1997) J. Am. Chem Soc. , vol.119 , pp. 681
    • Kim, C.U.1    Lew, W.2    Williams, M.A.3    Liu, H.4    Zhang, L.5    Swaminathan, S.6    Bischofberger, N.7    Chen, M.S.8    Mendel, D.B.9    Tai, C.Y.10    Laver, W.G.11    Stevens, R.C.12
  • 30
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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.
    • (1995) J. Am. Chem. Soc. , vol.116 , pp. 1616
    • Sabesan, S.1    Neira, S.2    Davidson, F.3    Duus, J.O.4    Bock, K.5
  • 33
    • 1542606707 scopus 로고    scopus 로고
    • Leaving out HOBT does not affect the yield of the reaction. It was used to suppress racemization
    • Leaving out HOBT does not affect the yield of the reaction. It was used to suppress racemization.
  • 34
    • 1542501980 scopus 로고    scopus 로고
    • We are currently studying the problems associated with coupling reactions involving 10
    • We are currently studying the problems associated with coupling reactions involving 10.
  • 39
    • 1542397164 scopus 로고    scopus 로고
    • 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
    • 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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