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Volumn 16, Issue 1, 2010, Pages 65-70

On the use of N-dicyclopropylmethyl aspartyl-glycine synthone for backbone amide protection

Author keywords

Acid labile dicyclopropylmethyl group; Asp gly sequence motif; Aspartimide formation; Backbone amide protection

Indexed keywords

2 HYDROXY 4 METHOXYBENZYL DERIVATIVE; 2,2,4,6,7 PENTAMETHYLDIHYDROBENZOFURANE 5 SULFONYL DERIVATIVE; AMIDE; AMINO TERMINAL TELOPEPTIDE; ASPARTIC ACID DERIVATIVE; ASPARTIMIDE; BENZOFURAN DERIVATIVE; BENZYL DERIVATIVE; BIOTIN DERIVATIVE; BIOTINYL ARGINYLGLUTAMINYLTYROSYLARGINYLLEUCYLISOLEUCYLVALYLHISTIDYLASPARAGINYLGLYCYLTYRO SYLCYSTEINYLASPARTYLARGINYLSERYLGLUTAMYLARGINYLASPARAGINYLLEUCINE; CARBONYL DERIVATIVE; DIPEPTIDE; ESTER DERIVATIVE; ETHER DERIVATIVE; GLYCINE DERIVATIVE; IMIDE; N DICYCLOPROPYLMETHYLASPARTYLGLYCINE DERIVATIVE; PEPTIDE; PEPTIDE DERIVATIVE; RESIN; TERT BUTYL ESTER DERIVATIVE; TERT BUTYL ETHER DERIVATIVE; TERT BUTYLOXYCARBONYL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 74749103178     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1196     Document Type: Article
Times cited : (5)

References (21)
  • 1
    • 0000875125 scopus 로고
    • Sequence dependence of aspartimide formation during 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis
    • Lauer JL, Fields CG, Fields GB. Sequence dependence of aspartimide formation during 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis. Lett. Pept. Sci. 1994; 1: 197-205.
    • (1994) Lett. Pept. Sci , vol.1 , pp. 197-205
    • Lauer, J.L.1    Fields, C.G.2    Fields, G.B.3
  • 4
    • 27144504450 scopus 로고    scopus 로고
    • The aspartimide problem in Fmoc-based SPPS. Part III
    • Mergler M, Dick F. The aspartimide problem in Fmoc-based SPPS. Part III. J. Pept. Sci. 2005; 11: 650-657.
    • (2005) J. Pept. Sci , vol.11 , pp. 650-657
    • Mergler, M.1    Dick, F.2
  • 6
    • 0000664191 scopus 로고
    • Conformational studies of poly(oxyethylene)-bound peptides and protein sequences
    • Pillai VNR, Mutter M. Conformational studies of poly(oxyethylene)-bound peptides and protein sequences. Acc. Chem. Res. 1981; 14: 122-130.
    • (1981) Acc. Chem. Res , vol.14 , pp. 122-130
    • Pillai, V.N.R.1    Mutter, M.2
  • 7
    • 37049087217 scopus 로고
    • A reversible protecting group for the amide bond in peptides.Use in the synthesis of difficult sequences
    • Johnson T, Quibell M,Owen D, Sheppard RC. A reversible protecting group for the amide bond in peptides.Use in the synthesis of difficult sequences. J. Chem. Soc., Chem. Commun. 1993; 4: 369-372.
    • (1993) J. Chem. Soc., Chem. Commun , vol.4 , pp. 369-372
    • Johnson, T.1    Quibell, M.2    Owen, D.3    Sheppard, R.C.4
  • 8
    • 4244061816 scopus 로고
    • Suppression of piperidine-mediated side product formation for Asp(OBut)-containing peptides by the use of N-(2-hydroxy-4-methoxybenzyl) (Hmb) backbone amide protection
    • Quibell M, Owen D, Packman LC, Johnson T. Suppression of piperidine-mediated side product formation for Asp(OBut)-containing peptides by the use of N-(2-hydroxy-4-methoxybenzyl) (Hmb) backbone amide protection. J. Chem. Soc., Chem. Commun. 1994; 20: 2343-2344.
    • (1994) J. Chem. Soc., Chem. Commun , vol.20 , pp. 2343-2344
    • Quibell, M.1    Owen, D.2    Packman, L.C.3    Johnson, T.4
  • 9
    • 0029171221 scopus 로고
    • N,O-bisFmoc derivatives of N-(2-hydroxy-4-methoxybenzyl)-amino acids: Useful intermediates in peptide synthesis
    • Johnson T, Quibell M, Sheppard RC. N,O-bisFmoc derivatives of N-(2-hydroxy-4-methoxybenzyl)-amino acids: useful intermediates in peptide synthesis. J. Pept. Sci. 1995; 1: 11-25.
    • (1995) J. Pept. Sci , vol.1 , pp. 11-25
    • Johnson, T.1    Quibell, M.2    Sheppard, R.C.3
  • 10
    • 0029135139 scopus 로고
    • N-2-hydroxy-4-methoxybenzyl (Hmb) backbone protection strategy prevents double aspartimide formation in a difficult peptide sequence
    • Packman LC. N-2-hydroxy-4-methoxybenzyl (Hmb) backbone protection strategy prevents double aspartimide formation in a difficult peptide sequence. Tetrahedron Lett. 1995; 36: 7523-7526.
    • (1995) Tetrahedron Lett , vol.36 , pp. 7523-7526
    • Packman, L.C.1
  • 12
    • 33646502359 scopus 로고    scopus 로고
    • Synthesis of difficult peptides free of aspartimide and related products, using peptoid methodology
    • Zahariev S, Guarnaccia C, Pongor CI, Quaroni L, Čemažar M, Pongor S. Synthesis of difficult peptides free of aspartimide and related products, using peptoid methodology. Tetrahedron Lett. 2006; 47: 4121-4124.
    • (2006) Tetrahedron Lett , vol.47 , pp. 4121-4124
    • Zahariev, S.1    Guarnaccia, C.2    Pongor, C.I.3    Quaroni, L.4    Čemažar, M.5    Pongor, S.6
  • 13
    • 0032847944 scopus 로고    scopus 로고
    • The synthesis of difficult peptides using 2-hydroxy-4-methoxybenzyl or pseudoproline amino acid building blocks: A comparative study
    • SampsonWR, Patsiouras H,Ede NJ.The synthesis of difficult peptides using 2-hydroxy-4-methoxybenzyl or pseudoproline amino acid building blocks: a comparative study. J. Pept. Sci. 1999; 5: 403-409.
    • (1999) J. Pept. Sci , vol.5 , pp. 403-409
    • Sampson, W.R.1    Patsiouras, H.2    Ede, N.J.3
  • 15
    • 0002151506 scopus 로고
    • Leicht abspaltbare Schutzgruppen für Säureamidfunktionen 1.Mitteilung.
    • Weygand F, Steglich W, Bjarnason J, Akhtar R, Khan M. Leicht abspaltbare Schutzgruppen für Säureamidfunktionen 1.Mitteilung. Tetrahedron Lett. 1966; 7: 3483-3487.
    • (1966) Tetrahedron Lett , vol.7 , pp. 3483-3487
    • Weygand, F.1    Steglich, W.2    Bjarnason, J.3    Akhtar, R.4    Khan, M.5
  • 16
    • 40749148059 scopus 로고    scopus 로고
    • Solid phase synthesis of cyclic peptides: Model studies involving i-(i+4) side chain-to-side chain cyclisation
    • Ruczyński J, Lewandowska B, Mucha P, Rekowski P. Solid phase synthesis of cyclic peptides: model studies involving i-(i+4) side chain-to-side chain cyclisation. J. Pept. Sci. 2008; 14: 335-341.
    • (2008) J. Pept. Sci , vol.14 , pp. 335-341
    • Ruczyński, J.1    Lewandowska, B.2    Mucha, P.3    Rekowski, P.4
  • 17
    • 0029943007 scopus 로고    scopus 로고
    • A new protecting group for aspartic acid that minimizes piperidine-catalyzed aspartimide formation in Fmoc solid phase peptide synthesis
    • Karlström A, Undén A. A new protecting group for aspartic acid that minimizes piperidine-catalyzed aspartimide formation in Fmoc solid phase peptide synthesis. Tetrahedron Lett. 1996; 37: 4243-4246.
    • (1996) Tetrahedron Lett , vol.37 , pp. 4243-4246
    • Karlström, A.1    Undén, A.2
  • 20
    • 74749091504 scopus 로고    scopus 로고
    • Henklein P, Röder R, Weißhoff H, Henklein P, Carpino LA. The Dcpm protecting group is a useful alternative to the Hmb residue. Abstracts of the 20th American Peptide Symposium, Montreal, Canada. Biopolymers (Peptide Science) 2007; 88: 636;
    • (a) Henklein P, Röder R, Weißhoff H, Henklein P, Carpino LA. The Dcpm protecting group is a useful alternative to the Hmb residue. Abstracts of the 20th American Peptide Symposium, Montreal, Canada. Biopolymers (Peptide Science) 2007; 88: 636;
  • 21
    • 66349122016 scopus 로고    scopus 로고
    • Henklein P, Röder R, Weißhoff H, Henklein P, Carpino LA. The Dcpm protecting group is a useful alternative to the Hmb residue. In Proceedings of the 20th American Peptidsymposium, Montreal, Canada. Adv. Exp. Med. Biol. 2009; 611: 247-248.
    • (b) Henklein P, Röder R, Weißhoff H, Henklein P, Carpino LA. The Dcpm protecting group is a useful alternative to the Hmb residue. In Proceedings of the 20th American Peptidsymposium, Montreal, Canada. Adv. Exp. Med. Biol. 2009; 611: 247-248.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.