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Volumn 62, Issue 20, 2006, Pages 4954-4978

A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BENZOIC ACID; GLYCOPEPTIDE; LACTOSE; MANNOSE; MANNOSIDE; PENTASACCHARIDE; SUGAR; THIOGLYCOSIDE; TRISACCHARIDE;

EID: 33646491913     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.080     Document Type: Article
Times cited : (34)

References (72)
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    • For the all-chemical and chemoenzymatic synthesis of high mannose-containing N-linked glycopeptides, see, for example:
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    • With modification of the original procedure from:
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    • Shaban, M.A.E.1    Jeanloz, R.W.2
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    • 0003463148 scopus 로고    scopus 로고
    • The catalytic use of sodium methoxide in methanol is referred to as the Zemplén de-O-acetylation, see:, Wiley, New York, NY p 154
    • The catalytic use of sodium methoxide in methanol is referred to as the Zemplén de-O-acetylation, see:. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis (1999), Wiley, New York, NY p 154
    • (1999) Protective Groups in Organic Synthesis
    • Greene, T.W.1    Wuts, P.G.M.2
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    • 33646480061 scopus 로고    scopus 로고
    • note
    • 2O) is needed to dehydrate the initial adduct (amide) into the phthalimide.
  • 61
    • 0032558464 scopus 로고    scopus 로고
    • For a brilliant example featuring the simultaneous removal of 17 benzyl groups, see:
    • For a brilliant example featuring the simultaneous removal of 17 benzyl groups, see:. Frick W., Bauer A., Bauer S., Wied S., and Müller G. Biochem. 37 (1998) 13421
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    • Frick, W.1    Bauer, A.2    Bauer, S.3    Wied, S.4    Müller, G.5
  • 64
    • 0025126474 scopus 로고
    • For analysis of the fine specificities of 11 mouse monoclonal antibodies reactive with H-type 2 blood group determinants see:
    • For analysis of the fine specificities of 11 mouse monoclonal antibodies reactive with H-type 2 blood group determinants see:. Furukawa K., Welt S., Yin B.W.T., Feickert H.-J., Takahashi T., Ueda R., and Lloyd K.O. Mol. Immunol. 27 (1990) 723
    • (1990) Mol. Immunol. , vol.27 , pp. 723
    • Furukawa, K.1    Welt, S.2    Yin, B.W.T.3    Feickert, H.-J.4    Takahashi, T.5    Ueda, R.6    Lloyd, K.O.7
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    • note
    • Actually, these data demonstrate that, in the very least, one of the two H-type 2 determinants in 3 is immunorecognized. They do not prove that both subunits are recognized, although this is presumably the case.
  • 70
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    • note
    • 3CN/TFA gradient. The first C-terminal amino acid was attached to the superacid-lable Fmoc-Rink Amide MBHA resin. The subsequent amino acids, which were introduced were protected as Thr(OtBu) and Asp(Dmab ester). Standard TFA-cleavage, Dmab- and Fmoc-removal (2% hydrazine in MeOH), and acetylation of the N-terminus yielded the desired peptides.
  • 71
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    • Prepared from lactal according to the procedure published by
    • Prepared from lactal according to the procedure published by. Schaubach R., Hemberger J., and Kinzy W. Liebigs Ann. Chem. 7 (1991) 607-614
    • (1991) Liebigs Ann. Chem. , vol.7 , pp. 607-614
    • Schaubach, R.1    Hemberger, J.2    Kinzy, W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.