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Volumn 12, Issue 5, 2012, Pages 479-490

One-pot/sequential native chemical ligation using N-Sulfanylethylanilide peptide

Author keywords

native chemical ligation; peptides; protein chemistry; sequential ligation; thioesters

Indexed keywords

CYSTEINE; ESTER; OXAZOLIDINONE DERIVATIVE; PEPTIDE; THIOL DERIVATIVE;

EID: 84867877538     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.201200007     Document Type: Article
Times cited : (37)

References (120)
  • 6
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    • Fmoc SPPS has won increasing popularity in the synthesis of wide varieties of peptides because the milder Fmoc strategy, without the use of TFA and HF required for Boc SPPS, is suitable both for peptides possessing acid-sensitive modifications such as O-glycosidic and/or phosphate residues and for standard automated peptide synthesizers. For a review of Fmoc-based synthesis of peptide thioesters, see:, F. Mende,;, O. Seitz, Angew. Chem. Int. Ed. 2011, 50, 1232-1240.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 1232-1240
    • Mende, F.1    Seitz, O.2
  • 7
    • 77956277702 scopus 로고    scopus 로고
    • Because standard SPPS is not always a reliable synthetic procedure for peptide fragments more than 40-50 residues, preparation of proteins with over 100 residues requires a sequential ligation of multiple small peptide fragments of up to 30-40 residues. For a review of sequential NCL protocols, see:, J. Y. Lee, D. Bang, Pept. Sci. 2010, 94, 441-447.
    • (2010) Pept. Sci. , vol.94 , pp. 441-447
    • Lee, J.Y.1    Bang, D.2
  • 8
    • 77956296752 scopus 로고    scopus 로고
    • For reviews of NCL-like reactions using unnatural β- or γ-sulfanylamino acids followed by desulfurization, see: a), H. Rohde, O. Seitz, Pept. Sci. 2010, 94, 551-559.
    • (2010) Pept. Sci. , vol.94 , pp. 551-559
    • Rohde, H.1    Seitz, O.2
  • 11
    • 0035977638 scopus 로고    scopus 로고
    • Ligation at Ala (a-g), Phe (h), Val (i, j), Lys (k, l), Thr (m), Leu (n, o), Gln (p) or their combination (q) using a corresponding sulfanyl (selenyl)amino acid followed by desulfurization (deselenization). About Pro site, see references [29] and [30]. a), L. Z. Yan, P. E. Dawson, J. Am. Chem. Soc. 2001, 123, 526-533.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 526-533
    • Yan, L.Z.1    Dawson, P.E.2
  • 28
    • 0033657692 scopus 로고    scopus 로고
    • Other ligation protocols at non-cysteinyl site. a), J. Offer, P. E. Dawson, Org. Lett. 1999, 2, 23-26.
    • (1999) Org. Lett. , vol.2 , pp. 23-26
    • Offer, J.1    Dawson, P.E.2
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    • 0033397158 scopus 로고    scopus 로고
    • c) S. Aimoto, Pept. Sci. 1999, 51, 247-265.
    • (1999) Pept. Sci. , vol.51 , pp. 247-265
    • Aimoto, S.1
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    • 33751407480 scopus 로고    scopus 로고
    • For recent literatures about the N-S acyl-transfer-mediated synthesis of peptide thioester except for the use of N-acyl-N-sulfanylethyl moieties (also see references [17], [22], [25-27]). a), H. Hojo, Y. Onuma, Y. Akimoto, Y. Nakahara, Tetrahedron Lett. 2007, 48, 25-28.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 25-28
    • Hojo, H.1    Onuma, Y.2    Akimoto, Y.3    Nakahara, Y.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.