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Volumn 51, Issue 46, 2012, Pages 11571-11575

An advance in the chemical synthesis of homogeneous N-linked glycopolypeptides by convergent aspartylation

Author keywords

aspartimide; aspartylation; glycopeptides; pseudoproline dipeptide; solid phase synthesis

Indexed keywords

ASPARTIMIDE; ASPARTYLATION; DIPEPTIDE; GLYCOPEPTIDES; SOLID PHASE SYNTHESIS;

EID: 84868568294     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201205038     Document Type: Article
Times cited : (73)

References (47)
  • 32
    • 84958159438 scopus 로고    scopus 로고
    • For recent improvements in the efficiency of the SPPS approach to glycopeptide synthesis, see
    • For recent improvements in the efficiency of the SPPS approach to glycopeptide synthesis, see:, C. Heinlein, D. V. Silva, A. Tröster, J. Schmidt, A. Gross, C. Unverzagt, Angew. Chem. 2011, 123, 6530
    • (2011) Angew. Chem. , vol.123 , pp. 6530
    • Heinlein, C.1    Silva, D.V.2    Tröster, A.3    Schmidt, J.4    Gross, A.5    Unverzagt, C.6
  • 43
    • 33845582386 scopus 로고    scopus 로고
    • Installation of the Leu-Ser pseudoproline dipeptide at the C-terminus served to minimize peptide aggregation.
    • Installation of the Leu-Ser pseudoproline dipeptide at the C-terminus served to minimize peptide aggregation:, F. García-Martín, P. White, R. Steinauer, S. Côté, J. Tulla-Puche, F. Albericio, Biopolymers 2006, 84, 566.
    • (2006) Biopolymers , vol.84 , pp. 566
    • García-Martín, F.1    White, P.2    Steinauer, R.3    Côté, S.4    Tulla-Puche, J.5    Albericio, F.6
  • 47
    • 80053602559 scopus 로고    scopus 로고
    • Another line of conjecture focuses on the possible inhibition of the amidic NH deprotonation step necessary for aspartamide formation. Perhaps the hydrogen of the aspartamide NH group is transferred to the adjacent amide of the (n+1) amino acid through a hydrogen bond (to N or O). The tertiary amide character of the pseudoproline engagement, would impede such a transfer to either the N or O atom. Clearly the question of the basis for the pseudoproline effect will be pursued by concerned research groups, including our own.
    • R. Subirõs-Funosas, A. El-Faham, F. Albericio, Tetrahedron 2011, 67, 8595. Another line of conjecture focuses on the possible inhibition of the amidic NH deprotonation step necessary for aspartamide formation. Perhaps the hydrogen of the aspartamide NH group is transferred to the adjacent amide of the (n+1) amino acid through a hydrogen bond (to N or O). The tertiary amide character of the pseudoproline engagement, would impede such a transfer to either the N or O atom. Clearly the question of the basis for the pseudoproline effect will be pursued by concerned research groups, including our own.
    • (2011) Tetrahedron , vol.67 , pp. 8595
    • Subirõs-Funosas, R.1    El-Faham, A.2    Albericio, F.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.