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Volumn 12, Issue 3, 2006, Pages 213-219

Optimized selective N-methylation of peptides on solid support

Author keywords

Mitsunobu; N methylamino acids; N methylated peptides; N methylation; N methylpeptides; O nitrobenzenesulfonyl protecting group; Solid phase synthesis

Indexed keywords

9 FLUORENYLMETHYL CHLOROFORMATE; AROMATIC AMINE; DIMETHYL SULFATE; LEUCINE; METHIONINE; NITROBENZENE DERIVATIVE; PEPTIDE DERIVATIVE; SOLVENT; SULFONAMIDE; SULFONE DERIVATIVE; TRIPEPTIDE;

EID: 33644799946     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.711     Document Type: Article
Times cited : (105)

References (44)
  • 1
    • 0007193238 scopus 로고    scopus 로고
    • Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides
    • DOI: 10.1021/cr950005s
    • Humphrey JM, Chamberlin PA. Chemical synthesis of natural product peptides: coupling methods for the incorporation of noncoded amino acids into peptides. Chem. Rev. 1997; 97: 2243-2266. DOI: 10.1021/cr950005s
    • (1997) Chem. Rev. , vol.97 , pp. 2243-2266
    • Humphrey, J.M.1    Chamberlin, P.A.2
  • 2
    • 0000314051 scopus 로고
    • Synthetic studies of biologically active marine cyclopeptides
    • Wipf P. Synthetic studies of biologically active marine cyclopeptides. Chem. Rev. 1995; 95: 2115-2134.
    • (1995) Chem. Rev. , vol.95 , pp. 2115-2134
    • Wipf, P.1
  • 3
    • 0000915203 scopus 로고
    • Bioactive sponge peptides
    • Fusetani N, Matsunaga S. Bioactive sponge peptides. Chem. Rev. 1993; 93: 1771-1791.
    • (1993) Chem. Rev. , vol.93 , pp. 1771-1791
    • Fusetani, N.1    Matsunaga, S.2
  • 4
    • 0021341035 scopus 로고
    • Synthesis of cyclosporine. 3. Total synthesis of cyclosporine-A and cyclosporine-H, 2 fungal metabolites isolated from the species Tolypocladium-inflatum gams
    • DOI: 10.1002/hlca.19840670220
    • Wenger RM. Synthesis of cyclosporine. 3. Total synthesis of cyclosporine-A and cyclosporine-H, 2 fungal metabolites isolated from the species Tolypocladium-inflatum gams. Helv. Chim. Acta 1984; 67: 502-525. DOI: 10.1002/hlca.19840670220
    • (1984) Helv. Chim. Acta , vol.67 , pp. 502-525
    • Wenger, R.M.1
  • 5
    • 0021912607 scopus 로고
    • Synthesis of cyclosporine and analogs: Structural requirements for immunosuppressive activity
    • DOI: 10.1002/anie.198500773
    • Wenger RM. Synthesis of cyclosporine and analogs: structural requirements for immunosuppressive activity. Angew. Chem., Int. Ed. Engl. 1985; 24: 77-85. DOI: 10.1002/anie.198500773
    • (1985) Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 77-85
    • Wenger, R.M.1
  • 9
    • 0024507836 scopus 로고
    • Synthesis of the cyclodepsipeptide nordidemnin-B, a cytotoxic minor product isolated from the sea tunicate Trididemnum-cyanophorum
    • Jouin P, Poncet J, Dufour MN, Pantaloni A, Castro B. Synthesis of the cyclodepsipeptide nordidemnin-B, a cytotoxic minor product isolated from the sea tunicate Trididemnum-cyanophorum. J. Org. Chem. 1989; 54: 617-627.
    • (1989) J. Org. Chem. , vol.54 , pp. 617-627
    • Jouin, P.1    Poncet, J.2    Dufour, M.N.3    Pantaloni, A.4    Castro, B.5
  • 10
    • 85023437139 scopus 로고
    • The didemnins: Biological properties, chemistry and total synthesis
    • Atta-ur-Rahman (ed). Elsevier: Amsterdam
    • Li W-R, Joullié MM. The didemnins: biological properties, chemistry and total synthesis. In Studies in Natural Products Chemistry, Vol. 10, Stereoselective Synthesis (Part F), Atta-ur-Rahman (ed). Elsevier: Amsterdam, 1992; 241-302.
    • (1992) Studiesin Natural Products Chemistry, Vol 10. Stereoselective Synthesis , Issue.PART F , pp. 241-302
    • Li, W.-R.1    Joullié, M.M.2
  • 11
    • 0030854642 scopus 로고    scopus 로고
    • Synthesis of a reduced ring analog of didemnin B
    • DOI: 10.1021/jo9623696
    • Ramanjulu IM, Ding X, Joullié MM. Synthesis of a reduced ring analog of didemnin B. J. Org. Chem. 1997; 62: 4961-4969. DOI: 10.1021/jo9623696
    • (1997) J. Org. Chem. , vol.62 , pp. 4961-4969
    • Ramanjulu, I.M.1    Ding, X.2    Joullié, M.M.3
  • 12
    • 85004878848 scopus 로고
    • N-Methyl peptides. 7. Conformational perturbations induced by N-methylation of model dipeptides
    • Vitoux B, Aubry A, Cung MT, Marraud M. N-Methyl peptides. 7. Conformational perturbations induced by N-methylation of model dipeptides. Int. J. Pept. Protein Res. 1986; 27: 617-632.
    • (1986) Int. J. Pept. Protein Res. , vol.27 , pp. 617-632
    • Vitoux, B.1    Aubry, A.2    Cung, M.T.3    Marraud, M.4
  • 14
    • 0032503564 scopus 로고    scopus 로고
    • Conformational analysis of reverse-turn constraints by N-methylation and N-hydroxylation of amide bonds in peptides and non-peptide mimetics
    • DOI: 10.1021/ja970855k
    • Takeuchi Y, Marshall GR. Conformational analysis of reverse-turn constraints by N-methylation and N-hydroxylation of amide bonds in peptides and non-peptide mimetics. J. Am. Chem. Soc. 1998; 120: 5363-5372. DOI: 10.1021/ja970855k
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5363-5372
    • Takeuchi, Y.1    Marshall, G.R.2
  • 15
    • 0029084673 scopus 로고
    • Macrocyclic peptidomimetics: Forcing peptides into bioactive conformations
    • Fairlie DP, Abbenante G, March DR. Macrocyclic peptidomimetics: forcing peptides into bioactive conformations. Curr. Med. Chem. 1995;2:654-686.
    • (1995) Curr. Med. Chem. , vol.2 , pp. 654-686
    • Fairlie, D.P.1    Abbenante, G.2    March, D.R.3
  • 16
    • 0030746698 scopus 로고    scopus 로고
    • Design of a potent combined pseudopeptide endothelin-A/endothelin-B receptor antagonist, Ac-DBhg(16)-Leu-Asp-Ile-[NMe]Ile-Trp(21) (PD 156252): Examination of its pharmacokinetic and spectral properties
    • DOI: 10.1021/jm970161m
    • Cody WL, He JX, Reily MD, Baleen SJ, Walker DM, Reyner EL, Stewart BH, Doherty AM. Design of a potent combined pseudopeptide endothelin-A/endothelin-B receptor antagonist, Ac-DBhg(16)-Leu-Asp-Ile-[NMe]Ile-Trp(21) (PD 156252): examination of its pharmacokinetic and spectral properties. J. Med. Chem. 1997; 40: 2228-2240. DOI: 10.1021/jm970161m
    • (1997) J. Med. Chem. , vol.40 , pp. 2228-2240
    • Cody, W.L.1    He, J.X.2    Reily, M.D.3    Baleen, S.J.4    Walker, D.M.5    Reyner, E.L.6    Stewart, B.H.7    Doherty, A.M.8
  • 20
    • 0017122834 scopus 로고
    • Effects of isolated N-methylated residues on conformational characteristics of polypeptides
    • DOI: 10.1002/bip.1976.360150814
    • Tonelli AE. Effects of isolated N-methylated residues on conformational characteristics of polypeptides. Biopolymers 1976; 16: 1615-1622. DOI: 10.1002/bip.1976.360150814
    • (1976) Biopolymers , vol.16 , pp. 1615-1622
    • Tonelli, A.E.1
  • 21
    • 0019128779 scopus 로고
    • Conformational energy studies on N-methylated analogs of thyrotropin releasing hormone, enkephalin, and luteinizing-hormone-releasing hormone
    • DOI: 10.1002/bip.1980.360191103
    • Manavalan P, Momany FA. Conformational energy studies on N-methylated analogs of thyrotropin releasing hormone, enkephalin, and luteinizing-hormone-releasing hormone. Biopolymers 1980; 19: 1943-1973. DOI: 10.1002/bip.1980.360191103
    • (1980) Biopolymers , vol.19 , pp. 1943-1973
    • Manavalan, P.1    Momany, F.A.2
  • 22
    • 0026625290 scopus 로고
    • N-Methylated analogs of Ac[Nle28,31]CCK(26-33) - Synthesis, activity, and receptor selectivity
    • Ron R, Gilon C, Hanani M, Vromen A, Selinger Z, Chorev M. N-Methylated analogs of Ac[Nle28,31]CCK(26-33) - synthesis, activity, and receptor selectivity. J. Med. Chem. 1992; 35: 2806-2811.
    • (1992) J. Med. Chem. , vol.35 , pp. 2806-2811
    • Ron, R.1    Gilon, C.2    Hanani, M.3    Vromen, A.4    Selinger, Z.5    Chorev, M.6
  • 24
    • 0013511786 scopus 로고
    • Neurokinin-B is a preferred agonist for a neuronal substance-P receptor and its action is antagonized by enkephalin
    • Laufer R, Wormser U, Friedman ZY, Gilon C, Chorev M, Selinger Z. Neurokinin-B is a preferred agonist for a neuronal substance-P receptor and its action is antagonized by enkephalin. Proc. Natl. Acad. Sci. U.S.A. 1985; 82: 7444-7448.
    • (1985) Proc. Natl. Acad. Sci. U.S.A. , vol.82 , pp. 7444-7448
    • Laufer, R.1    Wormser, U.2    Friedman, Z.Y.3    Gilon, C.4    Chorev, M.5    Selinger, Z.6
  • 25
    • 0022856128 scopus 로고
    • Characterization of a neurokinin-B receptor-site in rat-brain using a highly selective radioligand
    • Laufer R, Gilon C, Chorev M, Selinger Z. Characterization of a neurokinin-B receptor-site in rat-brain using a highly selective radioligand. J. Biol. Chem. 1986; 261: 257-263.
    • (1986) J. Biol. Chem. , vol.261 , pp. 257-263
    • Laufer, R.1    Gilon, C.2    Chorev, M.3    Selinger, Z.4
  • 26
    • 0035848569 scopus 로고    scopus 로고
    • Highly potent and subtype selective ligands derived by N-methyl scan of a somatostatin antagonist
    • DOI: 10.1021/jm0005048
    • Rajeswaran WJ, Hocart SJ, Murphy WA. Highly potent and subtype selective ligands derived by N-methyl scan of a somatostatin antagonist. J. Med. Chem. 2001; 44: 1305-1311. DOI: 10.1021/jm0005048
    • (2001) J. Med. Chem. , vol.44 , pp. 1305-1311
    • Rajeswaran, W.J.1    Hocart, S.J.2    Murphy, W.A.3
  • 27
    • 0035953312 scopus 로고    scopus 로고
    • N-Methyl scan of somatostatin octapeptide agonists produces interesting effects on receptor subtype specificity
    • DOI: 10.1021/jm000361p
    • Rajeswaran WJ, Hocart SJ, Murphy WA. N-Methyl scan of somatostatin octapeptide agonists produces interesting effects on receptor subtype specificity. J. Med. Chem. 2001; 44: 1416-1421. DOI: 10.1021/jm000361p
    • (2001) J. Med. Chem. , vol.44 , pp. 1416-1421
    • Rajeswaran, W.J.1    Hocart, S.J.2    Murphy, W.A.3
  • 29
    • 0029014960 scopus 로고
    • Structure-activity-relationships of dermorphin analogs containing N-substituted amino-acids in the 2-position of the peptide sequence
    • Schmidt R, Kalman A, Chung NN, Lemieux C, Horvath C, Schiller PW. Structure-activity-relationships of dermorphin analogs containing N-substituted amino-acids in the 2-position of the peptide sequence. Int. J. Pept. Protein Res. 1995; 46: 47-55.
    • (1995) Int. J. Pept. Protein Res. , vol.46 , pp. 47-55
    • Schmidt, R.1    Kalman, A.2    Chung, N.N.3    Lemieux, C.4    Horvath, C.5    Schiller, P.W.6
  • 30
    • 0028796640 scopus 로고
    • Solid-phase synthesis of cyclosporine peptides
    • and references cited therein
    • Angell YM, Thomas TL, Flentke GR, Rich DH. Solid-phase synthesis of cyclosporine peptides. J. Am. Chem. Soc. 1995; 117: 7279-7280 and references cited therein.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 7279-7280
    • Angell, Y.M.1    Thomas, T.L.2    Flentke, G.R.3    Rich, D.H.4
  • 32
    • 20844455294 scopus 로고    scopus 로고
    • Convenient synthesis of N-methylamino acids compatible with Fmoc solid-phase peptide synthesis
    • published ASAP on-line May 20th 2005: DOI: 10.1021/jo050477z
    • Biron E, Kessler H. Convenient synthesis of N-methylamino acids compatible with Fmoc solid-phase peptide synthesis. J. Org. Chem. 2005; 70: 5183-5189, published ASAP on-line May 20th 2005: DOI: 10.1021/jo050477z
    • (2005) J. Org. Chem. , vol.70 , pp. 5183-5189
    • Biron, E.1    Kessler, H.2
  • 33
    • 0030936620 scopus 로고    scopus 로고
    • Site-selective N-methylation of peptides on solid support
    • DOI: 10.1021/ja9635443
    • Miller SC, Scanlan TS. Site-selective N-methylation of peptides on solid support. J. Am. Chem. Soc. 1997; 119: 2301-2302. DOI: 10.1021/ja9635443
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2301-2302
    • Miller, S.C.1    Scanlan, T.S.2
  • 34
    • 0032565117 scopus 로고    scopus 로고
    • oNBS-SPPS: A new method for solid-phase peptide synthesis
    • DOI: 10.1021/ja974252k
    • Miller SC, Scanlan TS. oNBS-SPPS: a new method for solid-phase peptide synthesis. J. Am. Chem. Soc. 1998; 120: 2690-2691. DOI: 10.1021/ja974252k
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2690-2691
    • Miller, S.C.1    Scanlan, T.S.2
  • 35
    • 0032485334 scopus 로고    scopus 로고
    • Site-specific N-alkylation of peptides on the solid phase
    • DOI: 10.1016/S0040-4039(97)10766-3
    • Reichwein JF, Liskamp MJ. Site-specific N-alkylation of peptides on the solid phase. Tetrahedron Lett. 1998; 39: 1243-1246. DOI: 10.1016/S0040-4039(97)10766-3
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1243-1246
    • Reichwein, J.F.1    Liskamp, M.J.2
  • 36
    • 0030820319 scopus 로고    scopus 로고
    • Solid phase synthesis of Fmoc N-methyl amino acids: Application of the fukuyama amine synthesis
    • DOI: 10.1016/S0040-4039(97)01774-7
    • Yang L, Chiu K. Solid phase synthesis of Fmoc N-methyl amino acids: application of the fukuyama amine synthesis. Tetrahedron Lett. 1997; 38: 7307-7310. DOI: 10.1016/S0040-4039(97)01774-7
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7307-7310
    • Yang, L.1    Chiu, K.2
  • 37
    • 0035902222 scopus 로고    scopus 로고
    • Direct mono-N-methylation of solid supported amino acids: A useful application of the matteson rearrangement of α-aminoalkylboronic esters
    • DOI: 10.1021/o10158031
    • Laplante C, Hall DG. Direct mono-N-methylation of solid supported amino acids: a useful application of the matteson rearrangement of α-aminoalkylboronic esters. Org. Lett. 2001; 3: 1487-1490. DOI: 10.1021/o10158031
    • (2001) Org. Lett. , vol.3 , pp. 1487-1490
    • Laplante, C.1    Hall, D.G.2
  • 38
    • 0029119899 scopus 로고
    • 2- and 4-Nitrobenzenesulfonamides: Exceptionally versatile means for preparation of secondary amines and protection of amines
    • DOI: 10.1016/0040-4039(95)01316-A
    • Fukuyama T, Jow C-K, Cheung M. 2- and 4-Nitrobenzenesulfonamides: exceptionally versatile means for preparation of secondary amines and protection of amines. Tetrahedron Lett. 1995; 36: 6373-6374. DOI: 10.1016/0040-4039(95)01316-A
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6373-6374
    • Fukuyama, T.1    Jow, C.-K.2    Cheung, M.3
  • 39
    • 14744281306 scopus 로고    scopus 로고
    • Solid-phase synthesis and characterization of N-methyl-rich peptides
    • DOI: 10.1111/j.1399-3011.2004.00213.x
    • Teixidó M, Albericio F, Giralt E. Solid-phase synthesis and characterization of N-methyl-rich peptides. J. Pept. Res. 2005; 65: 153-166. DOI: 10.1111/j.1399-3011.2004.00213.x
    • (2005) J. Pept. Res. , vol.65 , pp. 153-166
    • Teixidó, M.1    Albericio, F.2    Giralt, E.3
  • 40
    • 0033041516 scopus 로고    scopus 로고
    • In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate and its utilization for difficult couplings in solid-phase peptide synthesis
    • DOI: 10.1034/j.1399-3011.1999.00049.x
    • Falb E, Yechezkel T, Salitra Y, Gilon C. In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate and its utilization for difficult couplings in solid-phase peptide synthesis. J. Pept. Res. 1999; 53: 507-517. DOI: 10.1034/j.1399-3011.1999.00049.x
    • (1999) J. Pept. Res. , vol.53 , pp. 507-517
    • Falb, E.1    Yechezkel, T.2    Salitra, Y.3    Gilon, C.4
  • 41
    • 0037007832 scopus 로고    scopus 로고
    • Total synthesis of the nematicidal cyclododecapeptide omphalotin A by using racemization-free triphosgene-mediated couplings in the solid phase
    • DOI: 10.1002/1521-3773(20020703)41:13(2307::AID-ANIE2307)3.0.CO;2-Y
    • Thern B, Rudolph J, Jung G. Total synthesis of the nematicidal cyclododecapeptide omphalotin A by using racemization-free triphosgene-mediated couplings in the solid phase. Angew. Chem., Int. Ed. Engl. 2002: 41: 2307-2309. DOI: 10.1002/1521-3773(20020703)41:13(2307::AID-ANIE2307)3.0.CO;2-Y
    • (2002) Angew. Chem., Int. Ed. Engl. , vol.41 , pp. 2307-2309
    • Thern, B.1    Rudolph, J.2    Jung, G.3
  • 42
    • 0037043020 scopus 로고    scopus 로고
    • Triphosgene as highly efficient reagent for the solid-phase coupling of N-alkylated amino acids - Total synthesis of cyclosporin O
    • DOI: 10.1016/S0040-4039(02)00657-3
    • Thern B, Rudolph J, Jung G. Triphosgene as highly efficient reagent for the solid-phase coupling of N-alkylated amino acids - total synthesis of cyclosporin O. Tetrahedron Lett. 2002; 43: 5013-5016. DOI: 10.1016/S0040-4039(02)00657-3
    • (2002) Tetrahedron Lett. , vol.43 , pp. 5013-5016
    • Thern, B.1    Rudolph, J.2    Jung, G.3
  • 43
    • 0037122171 scopus 로고    scopus 로고
    • Efficient, racemization-free peptide coupling of N-alkyl amino acids by using amino acid chlorides generated in situ - Total syntheses of the cyclopeptides cyclosporin O and omphalotin A
    • DOI: 10.1002/anie.200290008
    • Sewald N. Efficient, racemization-free peptide coupling of N-alkyl amino acids by using amino acid chlorides generated in situ - total syntheses of the cyclopeptides cyclosporin O and omphalotin A. Angew. Chem., Int. Ed. Engl. 2002; 41: 4661-4663. DOI: 10.1002/anie.200290008
    • (2002) Angew. Chem., Int. Ed. Engl. , vol.41 , pp. 4661-4663
    • Sewald, N.1
  • 44
    • 0025232814 scopus 로고
    • Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids
    • Fields GB, Noble RL. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int. J. Pept. Protein Res. 1990; 35: 161-214.
    • (1990) Int. J. Pept. Protein Res. , vol.35 , pp. 161-214
    • Fields, G.B.1    Noble, R.L.2


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