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Volumn 12, Issue 12, 2011, Pages 1840-1844

N-Sulfanylethylanilide Peptide as a Crypto-Thioester Peptide

Author keywords

Kinetically controlled NCL; N S acyl transfer; Native chemical ligation; Peptides; Thioester peptide

Indexed keywords

ANILIDE; SULFUR DERIVATIVE; THIOESTER;

EID: 79961116621     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201100241     Document Type: Article
Times cited : (104)

References (47)
  • 36
    • 79961118532 scopus 로고    scopus 로고
    • While conducting this work, a bis(sulfanylethyl)amine-type unit was reported to behave as a thioester: see, ref. [5m-o].
    • While conducting this work, a bis(sulfanylethyl)amine-type unit was reported to behave as a thioester: see, ref. [5m-o].
  • 41
    • 33646728877 scopus 로고    scopus 로고
    • Across a concentration range of 10 to 200 mM of MPAA, NCLs proceeded at similar reaction rates. Although the intramolecular N-S acyl transfer of SEAlide peptides under neutral conditions was not observed in the absence of thiols, addition of a large excess amount of MPAA (100 equiv) to the solution of 1a in Gn{dot operator}HCl [6M, Na phosphate (0.2m), TCEP (30 mm), pH 7.4] induced the formation of the corresponding MPAA thioester in up to about 10% conversion ratio after 6 h.
    • E. C. B. Johnson, S. B. H. Kent, J. Am. Chem. Soc. 2006, 128, 6640-6646. Across a concentration range of 10 to 200 mM of MPAA, NCLs proceeded at similar reaction rates. Although the intramolecular N-S acyl transfer of SEAlide peptides under neutral conditions was not observed in the absence of thiols, addition of a large excess amount of MPAA (100 equiv) to the solution of 1a in Gn{dot operator}HCl [6M, Na phosphate (0.2m), TCEP (30 mm), pH 7.4] induced the formation of the corresponding MPAA thioester in up to about 10% conversion ratio after 6 h.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 6640-6646
    • Johnson, E.C.B.1    Kent, S.B.H.2
  • 42
    • 37349094422 scopus 로고    scopus 로고
    • Replacement of MPAA (an arylthiol) with sulfanylethylsulfonic acid (an alkylthiol) induced side reactions in the presence of TCEP, including desulfurization at cysteine and SEAlide moieties. See, and references cited herein.
    • Replacement of MPAA (an arylthiol) with sulfanylethylsulfonic acid (an alkylthiol) induced side reactions in the presence of TCEP, including desulfurization at cysteine and SEAlide moieties. See: Q. Wan, S. J. Danishefsky, Angew. Chem. 2007, 119, 9408-9412; Angew. Chem. Int. Ed. 2007, 46, 9248-9252; and references cited herein.
    • (2007) Angew. Chem. 2007, 119, 9408-9412; Angew. Chem. Int. Ed. , vol.46 , pp. 9248-9252
    • Wan, Q.1    Danishefsky, S.J.2
  • 44
    • 79961108305 scopus 로고    scopus 로고
    • Note
    • Although we have yet to elucidate the role of phosphate ions in the ligation, one potential explanation for the effect of phosphate is that the salt efficiently catalyzes proton transfer to accelerate the N-S acyl transfer, possibly involving a cyclic intermediate as shown below.
  • 45
    • 79961120340 scopus 로고    scopus 로고
    • Note
    • The N-S acyl transfer under acidic conditions (4M HCl in DMF) of a chiral amino acid-incorporated SEAlide peptide such as 1b is accompanied by partial racemization; however, the N-S acyl transfer followed by NCL under neutral conditions affords no racemization (Figure S7 in the Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.