메뉴 건너뛰기




Volumn 18, Issue 5, 2013, Pages 5155-5162

Understanding acid lability of cysteine protecting groups

Author keywords

Acid lability; Benzyl; Carbocation stability; Cys protecting groups; Diphenylmethyl (Dpm); Peptide synthesis

Indexed keywords

CYSTEINE; PEPTIDE;

EID: 84878276795     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18055155     Document Type: Article
Times cited : (15)

References (21)
  • 2
    • 84870578904 scopus 로고    scopus 로고
    • Eco-friendly combination of the immobilized PGA enzyme and the s-phacm protecting group for the synthesis of cys-containing peptides
    • Góngora-Benítez, M.; Basso, A.; Bruckdorfer, T.; Royo, M.; Tulla-Puche, J.; Albericio, F. Eco-Friendly Combination of the Immobilized PGA Enzyme and the S-Phacm Protecting Group for the Synthesis of Cys-Containing Peptides. Chem. Eur. J. 2012, 18, 16166-16176.
    • (2012) Chem. Eur. J , vol.18 , pp. 16166-16176
    • Góngora-Benítez, M.1    Basso, A.2    Bruckdorfer, T.3    Royo, M.4    Tulla-Puche, J.5    Albericio, F.6
  • 3
    • 84868365656 scopus 로고    scopus 로고
    • Trimethoxyphenylthio as a highly labile replacement for tert-butylthio cysteine protection in Fmoc solid phase synthesis
    • Postma, T.M.; Giraud, M.; Albericio, F. Trimethoxyphenylthio as a highly labile replacement for tert-butylthio cysteine protection in Fmoc solid phase synthesis. Org. Lett. 2012, 14, 5468-5471.
    • (2012) Org. Lett. , vol.14 , pp. 5468-5471
    • Postma, T.M.1    Giraud, M.2    Albericio, F.3
  • 4
    • 0000307708 scopus 로고
    • A new method for the protection of the sulfhydryl group during peptide synthesis
    • Akabori, S.; Sakakibara, S.; Shimonishi, Y.; Nabuhara, Y. A New Method for the Protection of the Sulfhydryl Group during Peptide Synthesis. Bull. Chem. Soc. Jpn. 1964, 37, 433-434.
    • (1964) Bull. Chem. Soc. Jpn , vol.37 , pp. 433-434
    • Akabori, S.1    Sakakibara, S.2    Shimonishi, Y.3    Nabuhara, Y.4
  • 5
    • 33847123581 scopus 로고    scopus 로고
    • Studies on deprotection of cysteine and selenocysteine side-chain protecting groups
    • DOI 10.1002/psc.795
    • Harris, K.M.; Flemer, S., Jr.; Hondal, R.J. Studies on deprotection of cysteine and selenocysteine side-chain protecting groups. J. Pept. Sci. 2007, 13, 81-93. (Pubitemid 46290944)
    • (2007) Journal of Peptide Science , vol.13 , Issue.2 , pp. 81-93
    • Harris, K.M.1    Flemer Jr., S.2    Hondal, R.J.3
  • 6
    • 0014915518 scopus 로고
    • Although, Dpm was first reported in the 70's by Photaki and co-workers in that moment its practical use in peptide synthesis was discarded because it was described the need of boiling TFA to remove it, probably due to the less effective scavenger applied
    • Although, Dpm was first reported in the 70's by Photaki and co-workers in that moment its practical use in peptide synthesis was discarded because it was described the need of boiling TFA to remove it, probably due to the less effective scavenger applied. Photaki, I.; Taylor-Papadimitrious, J.; Sakarellos, C.; Mazarakis, P.; Zervas, L. J. Chem. Soc. 1970, 2683.
    • (1970) J. Chem. Soc , pp. 2683
    • Photaki, I.1    Taylor-Papadimitrious, J.2    Sakarellos, C.3    Mazarakis, P.4    Zervas, L.5
  • 8
    • 0033574590 scopus 로고    scopus 로고
    • Linkers for solid phase organic synthesis
    • James, I.A. Linkers for solid phase organic synthesis. Tetrahedron 1999, 55, 4855-4946.
    • (1999) Tetrahedron , vol.55 , pp. 4855-4946
    • James, I.A.1
  • 9
    • 0033683359 scopus 로고    scopus 로고
    • Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry
    • Guillier, F.; Orain, D.; Bradley, M. Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry. Chem. Rev. 2000, 100, 2091-2157.
    • (2000) Chem. Rev. , vol.100 , pp. 2091-2157
    • Guillier, F.1    Orain, D.2    Bradley, M.3
  • 10
    • 0004539756 scopus 로고
    • The balance of steric and conjugative effects in phenyl-substituted cations, radicals, and anions
    • Hoffman, R.; Bissell, R.; Farnum, D.G. The balance of steric and conjugative effects in phenyl-substituted cations, radicals, and anions. J. Phys. Chem. 1969, 73, 1789-1800.
    • (1969) J. Phys. Chem. , vol.73 , pp. 1789-1800
    • Hoffman, R.1    Bissell, R.2    Farnum, D.G.3
  • 11
    • 0000268440 scopus 로고    scopus 로고
    • Benzyl, 9-fluorenyl and diphenylmethyl cations: Structures and relative stabilities based on hydride transfer reactions
    • DOI 10.1016/0166-1280(95)04445-0
    • Rodriguez, C.F.; Vucković, D.L.; Hopkinson, A.C. Benzyl, 9-fluorenyl and diphenylmethyl cations: Structures and relative stabilities based on hydride transfer reactions. J. Mol. Struct. (Theochem) 1996, 363, 131-138. (Pubitemid 126371882)
    • (1996) Journal of Molecular Structure: THEOCHEM , vol.363 , Issue.2 , pp. 131-138
    • Rodriquez, C.F.1    Vuckovic, D.Lj.2    Hopkinson, A.C.3
  • 12
    • 33645022124 scopus 로고    scopus 로고
    • Correlation between Hammett substituent constants and directly calculated π-conjugation strength
    • Fernández, I.; Frenking, G. Correlation between Hammett substituent constants and directly calculated π-conjugation strength. J. Org. Chem. 2006, 71, 2251-2256.
    • (2006) J. Org. Chem. , vol.71 , pp. 2251-2256
    • Fernández, I.1    Frenking, G.2
  • 14
    • 0026896119 scopus 로고
    • 4-Methyltrityl (Mtt): A new protecting group for the side chain protection of Asn and Gln in solid-phase peptide synthesis
    • Sax, B.; Dick, F.; Tanner, R.; Gosteli, J. 4-Methyltrityl (Mtt): A new protecting group for the side chain protection of Asn and Gln in solid-phase peptide synthesis. Pept. Res. 1992, 5, 245-246.
    • (1992) Pept. Res , vol.5 , pp. 245-246
    • Sax, B.1    Dick, F.2    Tanner, R.3    Gosteli, J.4
  • 15
    • 0001525365 scopus 로고    scopus 로고
    • α-9-Fluorenylmethyloxycarbonyl (Fmoc) Strategy of Peptide Synthesis
    • Han, Y.; Barany, G. Novel S-Xanthenyl Protecting Groups for Cysteine and Their Applications for the Nα-9-Fluorenylmethyloxycarbonyl (Fmoc) Strategy of Peptide Synthesis. J. Org. Chem. 1997, 62, 3841-3848. (Pubitemid 127494795)
    • (1997) Journal of Organic Chemistry , vol.62 , Issue.12 , pp. 3841-3848
    • Han, Y.1    Barany, G.2
  • 16
    • 0026772188 scopus 로고
    • S-2,4,6-trimethoxybenzyl (Tmob): A novel cysteine protecting group for the Nα-(9-fluorenylmethoxycarbonyl) (Fmoc) strategy of peptide synthesis
    • Munson, M.C.; Garcia-Echeverria, C.; Albericio, F.; Barany, G. S-2,4,6-trimethoxybenzyl (Tmob): A novel cysteine protecting group for the Nα-(9-fluorenylmethoxycarbonyl) (Fmoc) strategy of peptide synthesis. J. Org. Chem. 1992, 57, 3013-3018.
    • (1992) J. Org. Chem , vol.57 , pp. 3013-3018
    • Munson, M.C.1    Garcia-Echeverria, C.2    Albericio, F.3    Barany, G.4
  • 17
    • 3042902605 scopus 로고
    • Sulfur-containing polypeptides. IV. Synthetic routes to cysteine peptides
    • Hiskey, R.G.; Adams, J.B. Sulfur-containing polypeptides. IV. Synthetic routes to cysteine peptides. J. Org. Chem. 1966, 31, 2178-2183.
    • (1966) J. Org. Chem. , vol.31 , pp. 2178-2183
    • Hiskey, R.G.1    Adams, J.B.2
  • 18
    • 77953860392 scopus 로고    scopus 로고
    • 2,2,4,6,7-Pentamethyl-2,3-dihydrobenzofuran-5-methyl (Pbfm) as an alternative to the trityl group for the side-chain protection of Cysteine and Asparagine/Glutamine
    • Garcia, O.; Bofill, J.M.; Nicolas, E.; Albericio, F. 2,2,4,6,7- Pentamethyl-2,3-dihydrobenzofuran-5-methyl (Pbfm) as an alternative to the trityl group for the side-chain protection of Cysteine and Asparagine/Glutamine. Eur. J. Org. Chem. 2010, 19, 3631-3640.
    • (2010) Eur. J. Org. Chem , vol.19 , pp. 3631-3640
    • Garcia, O.1    Bofill, J.M.2    Nicolas, E.3    Albericio, F.4
  • 19
    • 22744450185 scopus 로고    scopus 로고
    • Substituent effects on the stability of extended benzylic carbocations: A computational study of conjugation
    • DOI 10.1039/b504967a
    • Pittelkow, M.; Christensen, J.B.; Sølling, T.I. Substituent effects on the stability of extended benzylic carbocations: A computational study of conjugation. Org. Biomol. Chem. 2005, 3, 2441-2449. (Pubitemid 41028054)
    • (2005) Organic and Biomolecular Chemistry , vol.3 , Issue.13 , pp. 2441-2449
    • Pittelkow, M.1    Christensen, J.B.2    Solling, T.I.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.