메뉴 건너뛰기




Volumn 21, Issue 3, 2015, Pages 201-207

Efficient generation of peptide hydrazides via direct hydrazinolysis of Peptidyl-Wang-TentaGel resins

Author keywords

hydrazinolysis; peptide hydrazides; peptide thioesters; solid phase peptide synthesis; Wang linker

Indexed keywords

AMINO ACID; HYDRAZIDE DERIVATIVE; OCTAPEPTIDE; PEPTIDE HYDRAZIDE DERIVATIVE; PHENOL; RESIN; THIOESTER; UNCLASSIFIED DRUG; FLUORENE DERIVATIVE; HYDRAZINE DERIVATIVE; N(ALPHA)-FLUORENYLMETHYLOXYCARBONYLAMINO ACIDS; OLIGOPEPTIDE; POLYSTYRENE DERIVATIVE; TENTAGEL RESIN; WANG RESIN;

EID: 84923647824     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2747     Document Type: Article
Times cited : (11)

References (43)
  • 2
    • 84888360087 scopus 로고    scopus 로고
    • Chemical synthesis of proteins using peptide hydrazides as thioester surrogates
    • Zheng J-S, Tang S, Qi Y-K, Wang Z-P, Liu L,. Chemical synthesis of proteins using peptide hydrazides as thioester surrogates. Nat. Protocols 2013; 8 (12): 2483-2495.
    • (2013) Nat. Protocols , vol.8 , Issue.12 , pp. 2483-2495
    • Zheng, J.-S.1    Tang, S.2    Qi, Y.-K.3    Wang, Z.-P.4    Liu, L.5
  • 3
    • 84867057855 scopus 로고    scopus 로고
    • Convergent chemical synthesis of proteins by ligation of peptide hydrazides
    • Fang GM, Wang JX, Liu L,. Convergent chemical synthesis of proteins by ligation of peptide hydrazides. Angew. Chem. Int. Ed. Engl. 2012; 51 (41): 10347-10350.
    • (2012) Angew. Chem. Int. Ed. Engl. , vol.51 , Issue.41 , pp. 10347-10350
    • Fang, G.M.1    Wang, J.X.2    Liu, L.3
  • 4
    • 62449282062 scopus 로고    scopus 로고
    • Total chemical synthesis of proteins
    • Kent SB,. Total chemical synthesis of proteins. Chem. Soc. Rev. 2009; 38 (2): 338-351.
    • (2009) Chem. Soc. Rev. , vol.38 , Issue.2 , pp. 338-351
    • Kent, S.B.1
  • 5
    • 57749121492 scopus 로고    scopus 로고
    • Chemoselective ligation and modification strategies for peptides and proteins
    • Hackenberger CP, Schwarzer D,. Chemoselective ligation and modification strategies for peptides and proteins. Angew. Chem. Int. Ed.Engl. 2008; 47 (52): 10030-10074.
    • (2008) Angew. Chem. Int. Ed.Engl. , vol.47 , Issue.52 , pp. 10030-10074
    • Hackenberger, C.P.1    Schwarzer, D.2
  • 6
    • 27944433008 scopus 로고    scopus 로고
    • Protein semi-synthesis: New proteins for functional and structural studies
    • Durek T, Becker CF,. Protein semi-synthesis: new proteins for functional and structural studies. Biomol. Eng. 2005; 22 (5-6): 153-172.
    • (2005) Biomol. Eng. , vol.22 , Issue.5-6 , pp. 153-172
    • Durek, T.1    Becker, C.F.2
  • 7
    • 0037548053 scopus 로고    scopus 로고
    • Semisynthesis of proteins by expressed protein ligation
    • Muir TW,. Semisynthesis of proteins by expressed protein ligation. Annu. Rev. Biochem. 2003; 72: 249-289.
    • (2003) Annu. Rev. Biochem. , vol.72 , pp. 249-289
    • Muir, T.W.1
  • 8
    • 52449107990 scopus 로고    scopus 로고
    • An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation
    • Blanco-Canosa JB, Dawson PE,. An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation. Angew. Chem. Int. Ed. Engl. 2008; 47 (36): 6851-6855.
    • (2008) Angew. Chem. Int. Ed. Engl. , vol.47 , Issue.36 , pp. 6851-6855
    • Blanco-Canosa, J.B.1    Dawson, P.E.2
  • 9
  • 10
    • 79851491503 scopus 로고    scopus 로고
    • Peptidyl N,N-bis(2-mercaptoethyl)-amides as thioester precursors for native chemical ligation
    • Hou W, Zhang X, Li F, Liu CF,. Peptidyl N,N-bis(2-mercaptoethyl)-amides as thioester precursors for native chemical ligation. Org. Lett. 2011; 13 (3): 386-389.
    • (2011) Org. Lett. , vol.13 , Issue.3 , pp. 386-389
    • Hou, W.1    Zhang, X.2    Li, F.3    Liu, C.F.4
  • 12
    • 79551670677 scopus 로고    scopus 로고
    • 9-Fluorenylmethoxycarbonyl-based solid-phase synthesis of peptide alpha-thioesters
    • Mende F, Seitz O,. 9-Fluorenylmethoxycarbonyl-based solid-phase synthesis of peptide alpha-thioesters. Angew. Chem. Int. Ed. Engl. 2011; 50 (6): 1232-1240.
    • (2011) Angew. Chem. Int. Ed. Engl. , vol.50 , Issue.6 , pp. 1232-1240
    • Mende, F.1    Seitz, O.2
  • 14
    • 77950338273 scopus 로고    scopus 로고
    • Sequential native chemical ligation utilizing peptide thioacids derived from newly developed Fmoc-based synthetic method
    • Shigenaga A, Sumikawa Y, Tsuda S, Sato K, Otaka A,. Sequential native chemical ligation utilizing peptide thioacids derived from newly developed Fmoc-based synthetic method. Tetrahedron 2010; 66 (18): 3290-3296.
    • (2010) Tetrahedron , vol.66 , Issue.18 , pp. 3290-3296
    • Shigenaga, A.1    Sumikawa, Y.2    Tsuda, S.3    Sato, K.4    Otaka, A.5
  • 15
    • 84888584889 scopus 로고    scopus 로고
    • Development of new thioester equivalents for protein chemical synthesis
    • Zheng JS, Tang S, Huang YC, Liu L,. Development of new thioester equivalents for protein chemical synthesis. Acc. Chem. Res. 2013; 46 (11): 2475-2484.
    • (2013) Acc. Chem. Res. , vol.46 , Issue.11 , pp. 2475-2484
    • Zheng, J.S.1    Tang, S.2    Huang, Y.C.3    Liu, L.4
  • 16
    • 0000803035 scopus 로고
    • Polypeptide-synthesis using the S-alkyl thioester of a partially protected peptide segment - Synthesis of the DNA-binding domain of C-Myb protein (142-193)-Nh2
    • Hojo H, Aimoto S,. Polypeptide-synthesis using the S-alkyl thioester of a partially protected peptide segment-synthesis of the DNA-binding domain of C-Myb protein (142-193)-Nh2. B. Chem. Soc. Jpn. 1991; 64 (1): 111-117.
    • (1991) B. Chem. Soc. Jpn. , vol.64 , Issue.1 , pp. 111-117
    • Hojo, H.1    Aimoto, S.2
  • 17
    • 0034023981 scopus 로고    scopus 로고
    • Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation
    • Clippingdale AB, Barrow CJ, Wade JD,. Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation. J. Pept. Sci. 2000; 6 (5): 225-234.
    • (2000) J. Pept. Sci. , vol.6 , Issue.5 , pp. 225-234
    • Clippingdale, A.B.1    Barrow, C.J.2    Wade, J.D.3
  • 18
    • 0032548051 scopus 로고    scopus 로고
    • Direct preparation of peptide thioesters using an Fmoc solid-phase method
    • Li XQ, Kawakami T, Aimoto S,. Direct preparation of peptide thioesters using an Fmoc solid-phase method. Tetrahedron Lett. 1998; 39 (47): 8669-8672.
    • (1998) Tetrahedron Lett. , vol.39 , Issue.47 , pp. 8669-8672
    • Li, X.Q.1    Kawakami, T.2    Aimoto, S.3
  • 19
    • 79953218412 scopus 로고    scopus 로고
    • Fmoc-based synthesis of peptide thioesters for native chemical ligation employing a tert-Butyl thiol linker
    • Raz R, Rademann J,. Fmoc-based synthesis of peptide thioesters for native chemical ligation employing a tert-Butyl thiol linker. Org. Lett. 2011; 13 (7): 1606-1609.
    • (2011) Org. Lett. , vol.13 , Issue.7 , pp. 1606-1609
    • Raz, R.1    Rademann, J.2
  • 20
    • 0033607759 scopus 로고    scopus 로고
    • Backbone amide linker (BAL) strategy for N-alpha-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of unprotected peptide p-nitroanilides and thioesters
    • Alsina J, Yokum TS, Albericio F, Barany G,. Backbone amide linker (BAL) strategy for N-alpha-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of unprotected peptide p-nitroanilides and thioesters. J. Org. Chem. 1999; 64 (24): 8761-8769.
    • (1999) J. Org. Chem. , vol.64 , Issue.24 , pp. 8761-8769
    • Alsina, J.1    Yokum, T.S.2    Albericio, F.3    Barany, G.4
  • 21
    • 0033572729 scopus 로고    scopus 로고
    • Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry
    • Ingenito R, Bianchi E, Fattori D, Pessi A,. Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry. J. Am. Chem. Soc. 1999; 121 (49): 11369-11374.
    • (1999) J. Am. Chem. Soc. , vol.121 , Issue.49 , pp. 11369-11374
    • Ingenito, R.1    Bianchi, E.2    Fattori, D.3    Pessi, A.4
  • 22
    • 0035903684 scopus 로고    scopus 로고
    • Fmoc-compatible solid-phase peptide synthesis of long C-terminal peptide thioesters
    • Sewing A, Hilvert D,. Fmoc-compatible solid-phase peptide synthesis of long C-terminal peptide thioesters. Angew. Chem. Int. Ed. Engl. 2001; 40 (18): 3395-3396.
    • (2001) Angew. Chem. Int. Ed. Engl. , vol.40 , Issue.18 , pp. 3395-3396
    • Sewing, A.1    Hilvert, D.2
  • 23
    • 70349931080 scopus 로고    scopus 로고
    • Fmoc solid-phase synthesis of C-terminal peptide thioesters by formation of a backbone pyroglutamyl imide moiety
    • Tofteng AP, Sorensen KK, Conde-Frieboes KW, Hoeg-Jensen T, Jensen KJ,. Fmoc solid-phase synthesis of C-terminal peptide thioesters by formation of a backbone pyroglutamyl imide moiety. Angew. Chem. Int. Ed. Engl. 2009; 48 (40): 7411-7414.
    • (2009) Angew. Chem. Int. Ed. Engl. , vol.48 , Issue.40 , pp. 7411-7414
    • Tofteng, A.P.1    Sorensen, K.K.2    Conde-Frieboes, K.W.3    Hoeg-Jensen, T.4    Jensen, K.J.5
  • 24
    • 84897476598 scopus 로고    scopus 로고
    • Facile synthesis of C-terminal peptide hydrazide and thioester of NY-ESO-1 (A39-A68) from an Fmoc-hydrazine 2-chlorotrityl chloride resin
    • Huang Y-C, Chen C-C, Li S-J, Gao S, Shi J, Li Y-M,. Facile synthesis of C-terminal peptide hydrazide and thioester of NY-ESO-1 (A39-A68) from an Fmoc-hydrazine 2-chlorotrityl chloride resin. Tetrahedron 2014; 70 (18): 2951-2955.
    • (2014) Tetrahedron , vol.70 , Issue.18 , pp. 2951-2955
    • Huang, Y.-C.1    Chen, C.-C.2    Li, S.-J.3    Gao, S.4    Shi, J.5    Li, Y.-M.6
  • 25
    • 84923682862 scopus 로고    scopus 로고
    • A photolabile linker for the solid-phase synthesis of peptide hydrazides and heterocycles
    • Qvortrup K, Komnatnyy VV, Nielsen TE,. A photolabile linker for the solid-phase synthesis of peptide hydrazides and heterocycles. Org. Lett. 2014; 16 (18): 4782-4785.
    • (2014) Org. Lett. , vol.16 , Issue.18 , pp. 4782-4785
    • Qvortrup, K.1    Komnatnyy, V.V.2    Nielsen, T.E.3
  • 26
    • 0001065230 scopus 로고
    • Solid-phase synthesis of protected peptide hydrazides. Preparation and application of hydroxymethyl resin and 3-(p-benzyloxyphenyl)-1,1-dimethylpropyloxycarbonylhydrazide resin
    • Wang S-S,. Solid-phase synthesis of protected peptide hydrazides. Preparation and application of hydroxymethyl resin and 3-(p-benzyloxyphenyl)-1,1-dimethylpropyloxycarbonylhydrazide resin. J. Org. Chem. 1975; 40 (9): 1235-1239.
    • (1975) J. Org. Chem. , vol.40 , Issue.9 , pp. 1235-1239
    • Wang, S.-S.1
  • 27
    • 0012297150 scopus 로고
    • Polymer-bound oxime esters as supports for solid-phase peptide-synthesis - Preparation of protected peptide-fragments
    • Degrado WF, Kaiser ET,. Polymer-bound oxime esters as supports for solid-phase peptide-synthesis-preparation of protected peptide-fragments. J. Org. Chem. 1980; 45 (7): 1295-1300.
    • (1980) J. Org. Chem. , vol.45 , Issue.7 , pp. 1295-1300
    • Degrado, W.F.1    Kaiser, E.T.2
  • 28
    • 0011484526 scopus 로고
    • Convenient synthesis of C-terminal peptide analogs by aminolysis of oxime resin-linked protected peptides
    • Lobl TJ, Maggiora LL,. Convenient synthesis of C-terminal peptide analogs by aminolysis of oxime resin-linked protected peptides. J. Org. Chem. 1988; 53 (9): 1979-1982.
    • (1988) J. Org. Chem. , vol.53 , Issue.9 , pp. 1979-1982
    • Lobl, T.J.1    Maggiora, L.L.2
  • 29
    • 0015931593 scopus 로고
    • p-Alkoxybenzyl alcohol resin and p-alkoxybenzyloxycarbonylhydrazide resin for solid phase synthesis of protected peptide fragments
    • Wang SS,. p-Alkoxybenzyl alcohol resin and p-alkoxybenzyloxycarbonylhydrazide resin for solid phase synthesis of protected peptide fragments. J. Am. Chem. Soc. 1973; 95 (4): 1328-1333.
    • (1973) J. Am. Chem. Soc. , vol.95 , Issue.4 , pp. 1328-1333
    • Wang, S.S.1
  • 31
    • 0014196430 scopus 로고
    • Removal of protected peptides by hydrazinolysis after solid-phase synthesis
    • Ohno M, Anfinsen CB,. Removal of protected peptides by hydrazinolysis after solid-phase synthesis. J. Am. Chem. Soc. 1967; 89 (23): 5994-5995.
    • (1967) J. Am. Chem. Soc. , vol.89 , Issue.23 , pp. 5994-5995
    • Ohno, M.1    Anfinsen, C.B.2
  • 32
    • 0016736971 scopus 로고
    • Preparation of protected peptide intermediates for a synthesis of the ovine pituitary growth hormone sequence 96-135
    • Wang S-S, Kulesha ID,. Preparation of protected peptide intermediates for a synthesis of the ovine pituitary growth hormone sequence 96-135. J. Org. Chem. 1975; 40 (9): 1227-1234.
    • (1975) J. Org. Chem. , vol.40 , Issue.9 , pp. 1227-1234
    • Wang, S.-S.1    Kulesha, I.D.2
  • 34
    • 84897696620 scopus 로고    scopus 로고
    • A quantitative and site-specific chemoenzymatic glycosylation approach for PEGylated MUC1 peptides
    • Bello C, Farbiarz K, Moller JF, Becker CFW, Schwientek T,. A quantitative and site-specific chemoenzymatic glycosylation approach for PEGylated MUC1 peptides. Chem. Sci. 2014; 5 (4): 1634-1641.
    • (2014) Chem. Sci. , vol.5 , Issue.4 , pp. 1634-1641
    • Bello, C.1    Farbiarz, K.2    Moller, J.F.3    Becker, C.F.W.4    Schwientek, T.5
  • 35
    • 0041783935 scopus 로고    scopus 로고
    • Native chemical ligation with aspartic and glutamic acids as C-terminal residues: Scope and limitations
    • Villain M, Gaertner H, Botti P,. Native chemical ligation with aspartic and glutamic acids as C-terminal residues: scope and limitations. Eur. J. Org Chem 2003; 17: 3267-3272.
    • (2003) Eur. J. Org Chem , vol.17 , pp. 3267-3272
    • Villain, M.1    Gaertner, H.2    Botti, P.3
  • 36
    • 84882257487 scopus 로고    scopus 로고
    • Native chemical ligation at Asx-Cys, Glx-Cys: Chemical synthesis and high-resolution X-ray structure of ShK toxin by racemic protein crystallography
    • Dang B, Kubota T, Mandal K, Bezanilla F, Kent SB,. Native chemical ligation at Asx-Cys, Glx-Cys: chemical synthesis and high-resolution X-ray structure of ShK toxin by racemic protein crystallography. J. Am. Chem. Soc. 2013; 135 (32): 11911-11919.
    • (2013) J. Am. Chem. Soc. , vol.135 , Issue.32 , pp. 11911-11919
    • Dang, B.1    Kubota, T.2    Mandal, K.3    Bezanilla, F.4    Kent, S.B.5
  • 37
    • 15544380011 scopus 로고
    • Über Peptidsynthesen, XXVIII 3. Mitteilung über Glukagon-Teilsequenzen Synthese der N-terminalen Glukagon-Teilsequenz 1-11
    • Schröder E,. Über Peptidsynthesen, XXVIII 3. Mitteilung über Glukagon-Teilsequenzen Synthese der N-terminalen Glukagon-Teilsequenz 1-11. Justus Liebigs Ann. Chem. 1965; 681: 231-240.
    • (1965) Justus Liebigs Ann. Chem. , vol.681 , pp. 231-240
    • Schröder, E.1
  • 38
    • 0014349489 scopus 로고
    • Side reactions in the synthesis of peptides containing the aspartylglycyl sequence
    • Ondetti MA, Deer A, Sheehan JT, Pluscec J, Kocy O,. Side reactions in the synthesis of peptides containing the aspartylglycyl sequence. Biochemistry 1968; 7 (11): 4069-4075.
    • (1968) Biochemistry , vol.7 , Issue.11 , pp. 4069-4075
    • Ondetti, M.A.1    Deer, A.2    Sheehan, J.T.3    Pluscec, J.4    Kocy, O.5
  • 39
    • 84885540182 scopus 로고
    • Die Synthese des β-Melanotropins (β-MSH) mit der Aminosäurensequenz des bovinen Hormons
    • Schwyzer R, Iselin B, Kappeler H, Riniker B, Rittel W, Zuber H,. Die Synthese des β-Melanotropins (β-MSH) mit der Aminosäurensequenz des bovinen Hormons. Helv. Chim. Acta 1963; 46 (6): 1975-1996.
    • (1963) Helv. Chim. Acta , vol.46 , Issue.6 , pp. 1975-1996
    • Schwyzer, R.1    Iselin, B.2    Kappeler, H.3    Riniker, B.4    Rittel, W.5    Zuber, H.6
  • 41
    • 0027519220 scopus 로고
    • 2-Phenyl isopropyl esters as carboxyl terminus protecting groups in the fast synthesis of peptide fragments
    • Yue C, Thierry J, Potier P,. 2-Phenyl isopropyl esters as carboxyl terminus protecting groups in the fast synthesis of peptide fragments. Tetrahedron Lett. 1993; 34: 323-326.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 323-326
    • Yue, C.1    Thierry, J.2    Potier, P.3
  • 43
    • 84923643539 scopus 로고    scopus 로고
    • Advances in the minimization of aspartimide formation
    • Behrendt R, Huber S, Mart R, White P,. Advances in the minimization of aspartimide formation. J. Pept. Sci. 2014; 20 (S1): S57-58.
    • (2014) J. Pept. Sci. , vol.20 , Issue.S1 , pp. S57-S58
    • Behrendt, R.1    Huber, S.2    Mart, R.3    White, P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.