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Volumn 53, Issue 1, 1997, Pages 369-390

Preparation of Tn and sialyl Tn building blocks used in Fmoc solid-phase synthesis of glycopeptide fragments from HIV gp120

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPROTEIN GP 120; VIRUS PROTEIN;

EID: 0031060570     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00992-1     Document Type: Article
Times cited : (83)

References (103)
  • 3
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    • Springer, G.F.1
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    • Simple mucin type O-glycans of HIV: Enzymatic prediction of glycosylation sites for vaccine construction
    • Bock, K.; Clausen, H. Eds.; Munksgaard: Copenhagen
    • Clausen, H.; Sørensen, T.; White, T.; Wandall, H. H.; Hansen, J. Simple mucin type O-glycans of HIV: Enzymatic prediction of glycosylation sites for vaccine construction. In Complex carbohydrates in drug research. Alfred Benzon Symposium 36.; Bock, K.; Clausen, H. Eds.; Munksgaard: Copenhagen, 1994; pp. 297-310.
    • (1994) Complex Carbohydrates in Drug Research. Alfred Benzon Symposium , vol.36 , pp. 297-310
    • Clausen, H.1    Sørensen, T.2    White, T.3    Wandall, H.H.4    Hansen, J.5
  • 19
    • 0002490637 scopus 로고
    • Glycopeptide synthesis
    • Lee, Y. C.; Lee, R. T. Eds.; Academic Press, Inc.: San Diego
    • Meldal, M. Glycopeptide synthesis. In Neoglycoconjugates: Preparation and applications; Lee, Y. C.; Lee, R. T. Eds.; Academic Press, Inc.: San Diego, 1994; pp. 145-198.
    • (1994) Neoglycoconjugates: Preparation and Applications , pp. 145-198
    • Meldal, M.1
  • 31
  • 37
    • 0343536683 scopus 로고    scopus 로고
    • note
    • 7Ga1α1,4Ga1β)QINSR, under identical experimental conditions, β-elimination (∼20%) was encountered when aspartic acid had been replaced by alanine, but not for the remaining glycopeptides in the series (S. Roy and J. Kihlberg, unpublished observations).
  • 40
    • 0343972548 scopus 로고    scopus 로고
    • note
    • 7Ga1β1,4Glcβ)QINSR using 20 mM NaOMe in MeOH (pH ≈ 11 on wet pH paper) resulted in predominant β-elimination and only minor amounts of the target glycopeptide could be isolated (P. Sjölin and J. Kihlberg, unpublished observations).
  • 41
    • 0000499264 scopus 로고
    • Stereocontrolled approaches to O-glycopeptide synthesis
    • Kovác, P. Ed.; American Chemical Society: Washington DC
    • Nakahara, Y.; Iijima, H.; Ogawa, T. Stereocontrolled approaches to O-glycopeptide synthesis. In Synthetic Oligosaccharides; Kovác, P. Ed.; American Chemical Society: Washington DC, 1994; pp. 249-266.
    • (1994) Synthetic Oligosaccharides , pp. 249-266
    • Nakahara, Y.1    Iijima, H.2    Ogawa, T.3
  • 55
    • 0343972545 scopus 로고    scopus 로고
    • note
    • However, cleavage of the TBDMS groups and silylation of excess glycosyl acceptor 6 was obtained when the reaction mixture from the glycosylation was applied to silica gel for purification by flash column chromatography. These side reactions could be avoided by addition of triethylamine to the reaction mixture after completion of the synthesis, and by inclusion of triethylamine in the eluants used for chromatography, but not by an aqueous work-up prior to purification.
  • 82
    • 0343536633 scopus 로고    scopus 로고
    • note
    • H-7,H-8 coupling constant, or on the chemical shift difference between the two hydrogens at C-9 in the sialic acid unit have been proposed for determination of the anomeric configuration of sialosides. However, these rules are not general as discussed in reference 74.
  • 90
    • 0343972519 scopus 로고    scopus 로고
    • unpublished observations
    • Kihlberg, J. unpublished observations.
    • Kihlberg, J.1
  • 91
    • 0343972518 scopus 로고    scopus 로고
    • note
    • It was not investigated if milder conditions, such as dilute methanolic sodium methoxide used for deacetylation of 20 in the preparation of 22, could have avoided the encountered side reactions.
  • 92
    • 0342666398 scopus 로고    scopus 로고
    • note
    • α-(fluoren-9-ylmethoxycarbonyl)-3-O-(2-acetamido-3,4,6-tri-O- acetyl-2-deoxy-α-D-galacto-pyranosyl)-L-threonine was used for preparation of the glycopeptides described in reference 17 without N-acetylation, suggesting that the phenomenon is somehow related to the sequence of the glycopeptide being prepared.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.