메뉴 건너뛰기




Volumn 1081, Issue , 2013, Pages 151-165

Solid-phase guanidinylation of peptidyl amines compatible with standard Fmoc-chemistry: Formation of monosubstituted guanidines

Author keywords

1 H pyrazole 1 carboxamidine; Depsipeptides; Fmoc solid phase peptide synthesis; Guanidinylation; Mukaiyama's reagent; N,N diisopropylcarbodiimide; N Iodosuccinimide; Thiourea; Triflylguanidine

Indexed keywords

AMINE; GUANIDINE DERIVATIVE;

EID: 84934444023     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-62703-652-8_10     Document Type: Article
Times cited : (6)

References (44)
  • 1
    • 15444365617 scopus 로고    scopus 로고
    • Recent developments in guanidinylating agents
    • Katritzky AR, Rogovoy BV (2005) Recent developments in guanidinylating agents. Arkivoc 4:49-87
    • (2005) Arkivoc , vol.4 , pp. 49-87
    • Katritzky, A.R.1    Rogovoy, B.V.2
  • 2
    • 0036899326 scopus 로고    scopus 로고
    • Solidphase synthesis of guanidinium derivatives from thiourea and isothiourea functionalities
    • Manimala JC, Eric V, Anslyn EV (2002) Solidphase synthesis of guanidinium derivatives from thiourea and isothiourea functionalities. Eur J Org Chem 2002:3909-3922
    • (2002) Eur J Org Chem , vol.2002 , pp. 3909-3922
    • Manimala, J.C.1    Eric, V.2    Anslyn, E.V.3
  • 3
    • 0034400884 scopus 로고    scopus 로고
    • The guanidine metabolites of and related compounds; Isolation and synthesis
    • Heys L, Moore CG, Murphy PJ (2000) The guanidine metabolites of and related compounds; Isolation and synthesis. Chem Soc Rev 29:57-67
    • (2000) Chem Soc Rev , vol.29 , pp. 57-67
    • Heys, L.1    Moore, C.G.2    Murphy, P.J.3
  • 4
    • 0029876296 scopus 로고    scopus 로고
    • Fusaricidin A, a new depsipeptide antibiotic produced by Bacillus polymyxa KT-8. Taxonomy, fermentation, isolation, structure elucidation and biological activity
    • Kajimura Y, Kaneda M (1996) Fusaricidin A, a new depsipeptide antibiotic produced by Bacillus polymyxa KT-8. Taxonomy, fermentation, isolation, structure elucidation and biological activity. J Antibiot 49:129-135
    • (1996) J Antibiot , vol.49 , pp. 129-135
    • Kajimura, Y.1    Kaneda, M.2
  • 5
    • 0030994849 scopus 로고    scopus 로고
    • Fusaricidins B, C and D, new depsipeptide antibiotics produced by Bacillus polymyxa KT-8: Isolation, structure elucidation and biological activity
    • Kajimura Y, Kaneda M (1997) Fusaricidins B, C and D, new depsipeptide antibiotics produced by Bacillus polymyxa KT-8: Isolation, structure elucidation and biological activity. J Antibiot 50:220-228
    • (1997) J Antibiot , vol.50 , pp. 220-228
    • Kajimura, Y.1    Kaneda, M.2
  • 6
    • 0023639028 scopus 로고
    • New peptide antibiotics LI-F03, F04, F05, F07, and F08, produced by Bacillus polymyxa. I. Isolation and characterization
    • Kurusu K, Ohba K (1987) New peptide antibiotics LI-F03, F04, F05, F07, and F08, produced by Bacillus polymyxa. I. Isolation and characterization. J Antibiot 40:1506-1514
    • (1987) J Antibiot , vol.40 , pp. 1506-1514
    • Kurusu, K.1    Ohba, K.2
  • 8
    • 0030764331 scopus 로고    scopus 로고
    • Structural requirements for potential Na/H exchange inhibitors obtained from quantitative structure-activity relationships of monocyclic and bicyclic aroylguanidines
    • Yamamoto T, Hori M, Watanabe I, Tsutsi H, Harada K, Ikeda S, Ohtaka H (1997) Structural requirements for potential Na/H exchange inhibitors obtained from quantitative structure-activity relationships of monocyclic and bicyclic aroylguanidines. Chem Pharm Bull 45:1282-1286
    • (1997) Chem Pharm Bull , vol.45 , pp. 1282-1286
    • Yamamoto, T.1    Hori, M.2    Watanabe, I.3    Tsutsi, H.4    Harada, K.5    Ikeda, S.6    Ohtaka, H.7
  • 9
    • 0031762538 scopus 로고    scopus 로고
    • Synthesis and quantitative structure-activity relationships of N-(3-oxo-3,4-dihydro-2Hbenzo[ 1,4]oxazine-6-carbonyl)guanidines as Na/H exchange inhibitors
    • Yamamoto T, Hori M, Watanabe I, Tsutsi H, Harada K, Ikeda S, Maruo T, Ohtaka H (1998) Synthesis and quantitative structure-activity relationships of N-(3-oxo-3,4-dihydro-2Hbenzo[ 1,4]oxazine-6-carbonyl)guanidines as Na/H exchange inhibitors. Chem Pharm Bull 46:1716-1723
    • (1998) Chem Pharm Bull , vol.46 , pp. 1716-1723
    • Yamamoto, T.1    Hori, M.2    Watanabe, I.3    Tsutsi, H.4    Harada, K.5    Ikeda, S.6    Maruo, T.7    Ohtaka, H.8
  • 10
    • 0032535563 scopus 로고    scopus 로고
    • Novel acylguanidine containing thrombin inhibitors with reduced basicity at the P1 moiety
    • Adang AE, Lucas H, de Man AP, Engh RA, Grootenhuis PD (1998) Novel acylguanidine containing thrombin inhibitors with reduced basicity at the P1 moiety. Bioorg Med Chem Lett 8:3603-3608
    • (1998) Bioorg Med Chem Lett , vol.8 , pp. 3603-3608
    • Adang, A.E.1    Lucas, H.2    De Man, A.P.3    Engh, R.A.4    Grootenhuis, P.D.5
  • 11
    • 0041654787 scopus 로고    scopus 로고
    • Aminoglycoside-derived cationic lipids for gene transfection: Synthesis of Kanamycin A derivatives
    • Sainlos M, Belmont P, Vigneron JP, Lehn P, Lehn JM (2003) Aminoglycoside-derived cationic lipids for gene transfection: synthesis of Kanamycin A derivatives. Eur J Org Chem 2003:2764-2774
    • (2003) Eur J Org Chem , vol.2003 , pp. 2764-2774
    • Sainlos, M.1    Belmont, P.2    Vigneron, J.P.3    Lehn, P.4    Lehn, J.M.5
  • 13
  • 14
    • 84864631153 scopus 로고    scopus 로고
    • Cell-penetrating peptides: Classes, origin, and current landscape
    • Milletti F (2012) Cell-penetrating peptides: classes, origin, and current landscape. Drug Discov Today 17(15-16):850-860
    • (2012) Drug Discov Today , vol.17 , Issue.15-16 , pp. 850-860
    • Milletti, F.1
  • 15
    • 65549133368 scopus 로고    scopus 로고
    • Delivery of macromolecules using arginine-rich cell-penetrating peptides: Ways to overcome endosomal entrapment
    • El-Sayed A, Futaki S, Harashima H (2009) Delivery of macromolecules using arginine-rich cell-penetrating peptides: ways to overcome endosomal entrapment. AAPS J 11:13-22
    • (2009) AAPS J , vol.11 , pp. 13-22
    • El-Sayed, A.1    Futaki, S.2    Harashima, H.3
  • 17
    • 0033794501 scopus 로고    scopus 로고
    • Polyarginine enters cells more efficiently than other polycationic homopolymers
    • Mitchell DJ, Kim DT, Steinman L, Fathman CG, Rothbard JB (2000) Polyarginine enters cells more efficiently than other polycationic homopolymers. J Pept Res 56:318-325
    • (2000) J Pept Res , vol.56 , pp. 318-325
    • Mitchell, D.J.1    Kim, D.T.2    Steinman, L.3    Fathman, C.G.4    Rothbard, J.B.5
  • 18
    • 0035937124 scopus 로고    scopus 로고
    • Argininerich peptides. An abundant source of membrane-permeable peptides having potential as carriers for intracellular protein delivery
    • Futaki S, Suzuki T, Ohashi W, Yagami T, Tanaka S, Ueda K, Sugiura Y (2001) Argininerich peptides. An abundant source of membrane-permeable peptides having potential as carriers for intracellular protein delivery. J Biol Chem 276:5836-5840
    • (2001) J Biol Chem , vol.276 , pp. 5836-5840
    • Futaki, S.1    Suzuki, T.2    Ohashi, W.3    Yagami, T.4    Tanaka, S.5    Ueda, K.6    Sugiura, Y.7
  • 19
    • 30044432598 scopus 로고    scopus 로고
    • Why is the Arg5-Glu13 salt bridge conserved in mammalian alpha-defensins?
    • Wu Z, de Leeuw E, Ericksen B, Lu W (2005) Why is the Arg5-Glu13 salt bridge conserved in mammalian alpha-defensins? J Biol Chem 280:43039-43047
    • (2005) J Biol Chem , vol.280 , pp. 43039-43047
    • Wu, Z.1    De Leeuw, E.2    Ericksen, B.3    Lu, W.4
  • 20
    • 0032007854 scopus 로고    scopus 로고
    • Cationic peptides: A new source of antibiotics
    • Hancock REW, Lehrer R (1998) Cationic peptides: a new source of antibiotics. Trends Biotechnol 16:82-88
    • (1998) Trends Biotechnol , vol.16 , pp. 82-88
    • Hancock, R.E.W.1    Lehrer, R.2
  • 21
    • 33745217570 scopus 로고    scopus 로고
    • The co-evolution of host cationic antimicrobial peptides and microbial resistance
    • Peschel A, Sahl HG (2006) The co-evolution of host cationic antimicrobial peptides and microbial resistance. Nat Rev Microbiol 4: 529-536
    • (2006) Nat Rev Microbiol , vol.4 , pp. 529-536
    • Peschel, A.1    Sahl, H.G.2
  • 22
    • 33750328939 scopus 로고    scopus 로고
    • A novel strategy for the solid-phase synthesis of cyclic lipodepsipeptides
    • Stawikowski M, Cudic P (2006) A novel strategy for the solid-phase synthesis of cyclic lipodepsipeptides. Tetrahedron Lett 47: 8587-8590
    • (2006) Tetrahedron Lett , vol.47 , pp. 8587-8590
    • Stawikowski, M.1    Cudic, P.2
  • 24
    • 0030948518 scopus 로고    scopus 로고
    • Solid phase synthesis of guanidines
    • Robinson S, Roskamp EJ (1997) Solid phase synthesis of guanidines. Tetrahedron 53:6697-6705
    • (1997) Tetrahedron , vol.53 , pp. 6697-6705
    • Robinson, S.1    Roskamp, E.J.2
  • 25
    • 0030581332 scopus 로고    scopus 로고
    • Solid phase synthesis of a diketopiperazine catalyst containing the unnatural amino acid (S)-norarginine
    • Kowalski J, Lipton MA (1996) Solid phase synthesis of a diketopiperazine catalyst containing the unnatural amino acid (S)-norarginine. Tetrahedron Lett 37:5839-5840
    • (1996) Tetrahedron Lett , vol.37 , pp. 5839-5840
    • Kowalski, J.1    Lipton, M.A.2
  • 26
    • 0000911184 scopus 로고    scopus 로고
    • Facile and efficient guanidinylation of amines using thioureas and mukaiyama's reagent
    • Yong YF, Kowalski JA, Lipton MA (1997) Facile and efficient guanidinylation of amines using thioureas and mukaiyama's reagent. J Org Chem 62:1540-1542
    • (1997) J Org Chem , vol.62 , pp. 1540-1542
    • Yong, Y.F.1    Kowalski, J.A.2    Lipton, M.A.3
  • 27
    • 0002237366 scopus 로고    scopus 로고
    • A new reagent for solid and solution phase synthesis of protected guanidines from amines
    • Yong YF, Kowalski JA, Thoen JC, Lipton MA (1999) A new reagent for solid and solution phase synthesis of protected guanidines from amines. Tetrahedron Lett 40:53-56
    • (1999) Tetrahedron Lett , vol.40 , pp. 53-56
    • Yong, Y.F.1    Kowalski, J.A.2    Thoen, J.C.3    Lipton, M.A.4
  • 28
    • 33751391460 scopus 로고
    • 1H-Pyrazole-1-carboxamidine hydrochloride an attractive reagent for guanidinylation of amines and its application to peptide synthesis
    • Bernatowicz MS, Wu Y, Matsueda GR (1992) 1H-Pyrazole-1-carboxamidine hydrochloride an attractive reagent for guanidinylation of amines and its application to peptide synthesis. J Org Chem 57:2497-2502
    • (1992) J Org Chem , vol.57 , pp. 2497-2502
    • Bernatowicz, M.S.1    Wu, Y.2    Matsueda, G.R.3
  • 29
    • 85081791243 scopus 로고    scopus 로고
    • A highly effective method for synthesis of Nω - substituted arginines. Peptides for new millenium
    • In: Fields GB, Tam JP, Barany G (ed). Kluver Academic, Dordrecht
    • Zakhariev S, Szekely Z, Guarnaccia C, Antcheva N, Pongor S (2000) A highly effective method for synthesis of Nω - substituted arginines. Peptides for new millenium. In: Fields GB, Tam JP, Barany G (ed) Proceedings of the 16th American peptide symposium. Kluver Academic, Dordrecht, pp 74-75
    • (2000) Proceedings of the 16th American Peptide Symposium , pp. 74-75
    • Zakhariev, S.1    Szekely, Z.2    Guarnaccia, C.3    Antcheva, N.4    Pongor, S.5
  • 31
    • 0025232814 scopus 로고
    • Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids
    • Fields GB, Noble RL (1990) Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int J Peptide Protein Res 35: 161-214
    • (1990) Int J Peptide Protein Res , vol.35 , pp. 161-214
    • Fields, G.B.1    Noble, R.L.2
  • 33
    • 0028361429 scopus 로고
    • A convenient preparation of monosubstituted N, N ′-di(Boc)- protected guanidines
    • Drake B, Patek M, Lebl M (1994) A convenient preparation of monosubstituted N, N ′-di(Boc)-protected guanidines. Synthesis 6:579-582
    • (1994) Synthesis , vol.6 , pp. 579-582
    • Drake, B.1    Patek, M.2    Lebl, M.3
  • 34
    • 0000735249 scopus 로고    scopus 로고
    • Diprotected triflylguanidines: A new class of guanidinylation reagents
    • Feichtinger K, Zapf C, Sings HL, Goodman M (1998) Diprotected triflylguanidines: a new class of guanidinylation reagents. J Org Chem 63:3804-3805
    • (1998) J Org Chem , vol.63 , pp. 3804-3805
    • Feichtinger, K.1    Zapf, C.2    Sings, H.L.3    Goodman, M.4
  • 35
    • 0032515126 scopus 로고    scopus 로고
    • Triurethane-protected guanidines and triflyldiurethane-protected guanidines: New reagents for guanidinylation reactions
    • Feichtinger K, Sings HL, Baker TJ, Matthews K, Goodman M (1998) Triurethane-protected guanidines and triflyldiurethane-protected guanidines: new reagents for guanidinylation reactions. J Org Chem 63:8432-8439
    • (1998) J Org Chem , vol.63 , pp. 8432-8439
    • Feichtinger, K.1    Sings, H.L.2    Baker, T.J.3    Matthews, K.4    Goodman, M.5
  • 36
    • 77955167910 scopus 로고    scopus 로고
    • Synthesis of guanidines from azides: A general and straightforward methodology in carbohydrate chemistry
    • Santana AG, Francisco CG, Suarez E, Gonzalez CC (2010) Synthesis of guanidines from azides: a general and straightforward methodology in carbohydrate chemistry. J Org Chem 75:5371-5374
    • (2010) J Org Chem , vol.75 , pp. 5371-5374
    • Santana, A.G.1    Francisco, C.G.2    Suarez, E.3    Gonzalez, C.C.4
  • 37
    • 0026467126 scopus 로고
    • A mild and efficient method for the preparation of guanidines
    • Poss MA, Iwanowicz E, Reid JA, Lin J, Gu Z (1992) A mild and efficient method for the preparation of guanidines. Tetrahedron Lett 33:5933-5936
    • (1992) Tetrahedron Lett , vol.33 , pp. 5933-5936
    • Poss, M.A.1    Iwanowicz, E.2    Reid, J.A.3    Lin, J.4    Gu, Z.5
  • 38
    • 0030936351 scopus 로고    scopus 로고
    • The HgCl 2-Promoted guanidinylation reaction: The scope and limitations
    • Levallet C, Lerpiniere J, Ko SY (1997) The HgCl 2-promoted guanidinylation reaction: the scope and limitations. Tetrahedron 53:5291-5304
    • (1997) Tetrahedron , vol.53 , pp. 5291-5304
    • Levallet, C.1    Lerpiniere, J.2    Ko, S.Y.3
  • 40
    • 0027371231 scopus 로고
    • Improved method for the preparation of guanidines
    • Kim KS, Qian L (1993) Improved method for the preparation of guanidines. Tetrahedron Lett 34:7677-7680
    • (1993) Tetrahedron Lett , vol.34 , pp. 7677-7680
    • Kim, K.S.1    Qian, L.2
  • 41
    • 0001773694 scopus 로고
    • A convenient method for the preparation of carbodiimides using 2-chloropyridinium salt
    • Shibanuma T, Shiono M, Mukaiyama T (1977) A convenient method for the preparation of carbodiimides using 2-chloropyridinium salt. Chem Lett 5:575-576
    • (1977) Chem Lett , vol.5 , pp. 575-576
    • Shibanuma, T.1    Shiono, M.2    Mukaiyama, T.3
  • 42
    • 1842788698 scopus 로고    scopus 로고
    • Preparation and evaluation of a polymersupported Mukaiyama reagent
    • Convers E, Tye H, Whittaker M (2004) Preparation and evaluation of a polymersupported Mukaiyama reagent. Tetrahedron Lett 45:3401-3404
    • (2004) Tetrahedron Lett , vol.45 , pp. 3401-3404
    • Convers, E.1    Tye, H.2    Whittaker, M.3
  • 43
    • 84981815927 scopus 로고
    • S-amination of thioureas and thiourethanes
    • Ley K, Eholzer U (1966) S-amination of thioureas and thiourethanes. Angew Chem Int Ed 5:674-674
    • (1966) Angew Chem Int Ed , vol.5 , pp. 674-674
    • Ley, K.1    Eholzer, U.2
  • 44
    • 59649109263 scopus 로고
    • Preparation of S-aminoisothioureas by nucleophilic substitution of S-chloroisothiocarbamoyl chlorides
    • Ottmann G, Hooks H (1967) Preparation of S-aminoisothioureas by nucleophilic substitution of S-chloroisothiocarbamoyl chlorides. Angew Chem Int Ed 6:1072-1073
    • (1967) Angew Chem Int Ed , vol.6 , pp. 1072-1073
    • Ottmann, G.1    Hooks, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.