메뉴 건너뛰기




Volumn , Issue 20, 2011, Pages 3247-3254

Hydantoin-free synthesis of peptide ester isocyanates, isothiocyanates, and dipeptidyl ureas: The application of zinc dust in a carbonylation procedure without base

Author keywords

base free synthesis; isothiocyanates; peptide ester isocyanates; peptidyl ureas; thioureas; zinc dust

Indexed keywords

ISOTHIOCYANATES; PEPTIDE AMIDES; ZINC DUST;

EID: 80053904540     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260216     Document Type: Article
Times cited : (9)

References (23)
  • 3
    • 84943896550 scopus 로고
    • Goldschmidt and Wick, who first attempted to synthesize these compounds by using gaseous phosgene at a temperature of 110 C, found that the formed isocyanate cyclized to hydantoin
    • Goldschmidt and Wick, who first attempted to synthesize these compounds by using gaseous phosgene at a temperature of 110 C, found that the formed isocyanate cyclized to hydantoin:, Goldschmidt S, Wick M, Justus Liebigs Ann. Chem. 1952 575 217
    • (1952) Justus Liebigs Ann. Chem. , vol.575 , pp. 217
    • Goldschmidt, S.1    Wick, M.2
  • 6
    • 0033546249 scopus 로고    scopus 로고
    • the base-catalyzed cyclization has constituted a main synthetic route for making peptide hydantoins
    • Chong P Y., Petillo P A., Tetrahedron Lett. 1999 40 4501; the base-catalyzed cyclization has constituted a main synthetic route for making peptide hydantoins
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4501
    • Chong, P.Y.1    Petillo, P.A.2
  • 10
    • 0032564614 scopus 로고    scopus 로고
    • For application of zinc as non-basic HCl scavenger for racemization free peptide coupling with Fmoc-amino acid chlorides, and for isolation of free amino acid methyl esters, see
    • For application of zinc as non-basic HCl scavenger for racemization free peptide coupling with Fmoc-amino acid chlorides, and for isolation of free amino acid methyl esters, see:, Sureshbabu V V., Gopi H N., Tetrahedron Lett. 1998 39 9769
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9769
    • Sureshbabu, V.V.1    Gopi, H.N.2
  • 12
    • 0028947941 scopus 로고
    • Due to difficulty in the addition of a stoichiometric quantity of the tertiary amine, excess base can be transferred. Presence of excess base can also promote several other side reactions which are intrinsic to peptides as substrates., Bednarek M A., Bodanszky M, Int. J. Pept. Protein Res. 1995 45 64; and references cited therein
    • (1995) Int. J. Pept. Protein Res. , vol.45 , pp. 64
    • Bednarek, M.A.1    Bodanszky, M.2
  • 15
    • 0032487770 scopus 로고    scopus 로고
    • An authentic sample of hydantoin was prepared from isocyanate 2a. To confirm the present protocol is free from hydantoin formation (see Supporting Information). Nefzi A., Ostresh J.M., Giultanotti M., Houghten R.A. Tetrahedron Lett., 1998 39 8199
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8199
    • Nefzi, A.1    Ostresh, J.M.2    Giultanotti, M.3    Houghten, R.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.