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Volumn 14, Issue 10, 2008, Pages 1084-1095

Pentapeptides containing two dehydrophenylalanine residues - Synthesis, structural studies and evaluation of their activity towards cathepsin C

Author keywords

Conformation; Dehydropeptide; Inhibitors of cathepsin C

Indexed keywords

DIPEPTIDYL PEPTIDASE I; GLYCYLPHENYLALANYLGLYCYLPHENYLALANYLGLYCINE; GLYCYLPHENYLALANYLGLYCYLPHENYLALANYLPHENYLALANINE; PENTAPEPTIDE; UNCLASSIFIED DRUG;

EID: 57849109453     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1045     Document Type: Article
Times cited : (21)

References (26)
  • 2
    • 0025817859 scopus 로고
    • Lantibiotics - ribosomally synthesized biologically active polypeptides containing sulfide bridges and α,β- didehydroaminoacids
    • Jung G. Lantibiotics - ribosomally synthesized biologically active polypeptides containing sulfide bridges and α,β- didehydroaminoacids. Angew. Chem. Int. Ed. Engl. 1991; 30: 1051-1068.
    • (1991) Angew. Chem. Int. Ed. Engl , vol.30 , pp. 1051-1068
    • Jung, G.1
  • 3
    • 0030024388 scopus 로고    scopus 로고
    • Solution strusture of dehydropeptides: A CD investigation
    • Pieroni O, Fissi A, Jain RM, Chauhan VS. Solution strusture of dehydropeptides: a CD investigation. Biopolymers 1996; 38: 97-108.
    • (1996) Biopolymers , vol.38 , pp. 97-108
    • Pieroni, O.1    Fissi, A.2    Jain, R.M.3    Chauhan, V.S.4
  • 4
    • 0014347799 scopus 로고
    • Stereochemical criteria for polypeptides and proteins. V. Conformation of a system of three linked peptide units
    • Venkatachalam CM. Stereochemical criteria for polypeptides and proteins. V. Conformation of a system of three linked peptide units. Biopolymers 1968; 6: 1425-1436.
    • (1968) Biopolymers , vol.6 , pp. 1425-1436
    • Venkatachalam, C.M.1
  • 5
    • 0015921220 scopus 로고
    • The synthesis of N-acyl-α- mercaptoalanine derivatives
    • Patel SM, Currie JO Jr, Olsen RK. The synthesis of N-acyl-α- mercaptoalanine derivatives J. Org. Chem. 1973; 38: 126-128.
    • (1973) J. Org. Chem , vol.38 , pp. 126-128
    • Patel, S.M.1    Currie Jr, J.O.2    Olsen, R.K.3
  • 6
    • 0000352433 scopus 로고
    • Design of helical motif using a,b-dehydrophenylalanine residues: Crystal structure of Boc-Val-dPhe-Phe-Ala-Phe-dPhe-Val-dPhe-Gly-OCH3, a 310-helical nonapeptide
    • Rajashankar KR, Ramakumar S, Chauhan VS. Design of helical motif using a,b-dehydrophenylalanine residues: Crystal structure of Boc-Val-dPhe-Phe-Ala-Phe-dPhe-Val-dPhe-Gly-OCH3, a 310-helical nonapeptide. J. Am. Chem. Soc. 1992; 114: 9225-9226.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 9225-9226
    • Rajashankar, K.R.1    Ramakumar, S.2    Chauhan, V.S.3
  • 7
    • 0025648829 scopus 로고
    • Crystal and molecular structure of Boc-D-Ala-delta Phe-Gly-delta Phe-D-Ala-OMe: A 3 10-helical dehydropeptide
    • Ciajolo MR, Tuzi A, Pratesi CR, Fissi A, Pieroni O. Crystal and molecular structure of Boc-D-Ala-delta Phe-Gly-delta Phe-D-Ala-OMe: a 3 10-helical dehydropeptide. Biopolymers 1990; 30: 911-920.
    • (1990) Biopolymers , vol.30 , pp. 911-920
    • Ciajolo, M.R.1    Tuzi, A.2    Pratesi, C.R.3    Fissi, A.4    Pieroni, O.5
  • 8
    • 0034012414 scopus 로고    scopus 로고
    • Synthesis of ΔEPhe- containing tripeptide via photoisomerisation and its conformation in solution
    • Inai Y, Kurashima S, Hirabayashi T, Yokota K. Synthesis of ΔEPhe- containing tripeptide via photoisomerisation and its conformation in solution. Biopolymers 2000; 53: 484-496.
    • (2000) Biopolymers , vol.53 , pp. 484-496
    • Inai, Y.1    Kurashima, S.2    Hirabayashi, T.3    Yokota, K.4
  • 10
    • 0028855326 scopus 로고
    • Sequence of Schistosoma mansoni cathepsin C and its structural comparison with papain and cathepsins B and L of the parasite
    • Butler R, Michel A, Kunz W, Klinkert MO. Sequence of Schistosoma mansoni cathepsin C and its structural comparison with papain and cathepsins B and L of the parasite. Protein Pept. Lett. 1995; 2: 313-320.
    • (1995) Protein Pept. Lett , vol.2 , pp. 313-320
    • Butler, R.1    Michel, A.2    Kunz, W.3    Klinkert, M.O.4
  • 12
    • 0005279948 scopus 로고
    • The synthesis and reactions of dehydro phenylalanine anilide
    • Breitholle AO, Stammer CH. The synthesis and reactions of dehydro phenylalanine anilide. Tetrahedron Lett. 1975; 28: 2381-2384.
    • (1975) Tetrahedron Lett , vol.28 , pp. 2381-2384
    • Breitholle, A.O.1    Stammer, C.H.2
  • 13
    • 0035061550 scopus 로고    scopus 로고
    • Synthesis of tetrapeptide p-nitrophenylanilides containing dehydroalanine and dehydrophenylalanine and their influence on cathepsin C activity
    • Makowski M, Pawełczak M, Latajka R, Nowak K, Kafarski P. Synthesis of tetrapeptide p-nitrophenylanilides containing dehydroalanine and dehydrophenylalanine and their influence on cathepsin C activity. J. Pept. Sci. 2001; 7: 141-145.
    • (2001) J. Pept. Sci , vol.7 , pp. 141-145
    • Makowski, M.1    Pawełczak, M.2    Latajka, R.3    Nowak, K.4    Kafarski, P.5
  • 14
    • 38949159145 scopus 로고    scopus 로고
    • Combined effect of the ΔPhe or ΔAla residue and the p- nitroanilide group on a dehydropeptides conformation
    • Lisowski M, Latajka R, Makowski M, Lis T, Picur B, Panek J, Kafarski P. Combined effect of the ΔPhe or ΔAla residue and the p- nitroanilide group on a dehydropeptides conformation. Biopolymers 2008; 89: 220-234.
    • (2008) Biopolymers , vol.89 , pp. 220-234
    • Lisowski, M.1    Latajka, R.2    Makowski, M.3    Lis, T.4    Picur, B.5    Panek, J.6    Kafarski, P.7
  • 15
    • 33745699013 scopus 로고    scopus 로고
    • Peptide p-nitrophenylanilides containing (E)- dehydrophenylalanine - synthesis, structural studies and evaluation of their activity towards cathepsin C
    • Latajka R, Makowski M, Jewginski M, Pawelczak M, Koroniak H, Kafarski P. Peptide p-nitrophenylanilides containing (E)- dehydrophenylalanine - synthesis, structural studies and evaluation of their activity towards cathepsin C. N. J. Chem. 2006; 30(7): 1009-1018.
    • (2006) N. J. Chem , vol.30 , Issue.7 , pp. 1009-1018
    • Latajka, R.1    Makowski, M.2    Jewginski, M.3    Pawelczak, M.4    Koroniak, H.5    Kafarski, P.6
  • 17
    • 33646265253 scopus 로고    scopus 로고
    • Stabilization of unusual structures in peptides using a,b-dehydrophenylalanine: Crystal and solution structures of Boc-Pro-ΔPhe-Val-ΔPhe-Ala-OMe and Boc-Pro-ΔPhe-Gly-ΔPhe- Ala-OMe
    • Mathyr P, Ramagopal UA, Ramakumar S, Jagannathan NR, Chauhan VS. Stabilization of unusual structures in peptides using a,b-dehydrophenylalanine: crystal and solution structures of Boc-Pro-ΔPhe-Val-ΔPhe-Ala-OMe and Boc-Pro-ΔPhe-Gly-ΔPhe- Ala-OMe. Biopolymers 2006; 84: 298-309.
    • (2006) Biopolymers , vol.84 , pp. 298-309
    • Mathyr, P.1    Ramagopal, U.A.2    Ramakumar, S.3    Jagannathan, N.R.4    Chauhan, V.S.5
  • 18
    • 2442449149 scopus 로고    scopus 로고
    • Synthesis and activity of phosphinic tripeptide inhibitors of cathepsin C
    • Mucha A, Pawelczak M, Hurek J, Kafarski P. Synthesis and activity of phosphinic tripeptide inhibitors of cathepsin C. Bioorg. Med. Chem. Lett. 2004; 14: 3113-3116.
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 3113-3116
    • Mucha, A.1    Pawelczak, M.2    Hurek, J.3    Kafarski, P.4
  • 19
    • 57849159273 scopus 로고    scopus 로고
    • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, HadaM, EharaM, ToyotaK, FukudaR, Hasegawa J, IshidaM, Nakajima T, Honda Y, Kitao O, Nakai H, KleneM, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Pople; Gaussian 03 Revision C.02, Gaussian, Inc: Wallingford, CT, 2004
    • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, HadaM, EharaM, ToyotaK, FukudaR, Hasegawa J, IshidaM, Nakajima T, Honda Y, Kitao O, Nakai H, KleneM, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Pople; Gaussian 03 (Revision C.02). Gaussian, Inc: Wallingford, CT, 2004.
  • 20
    • 17944366493 scopus 로고    scopus 로고
    • Structure of human dipeptidyl peptidase I (cathepsin C): Exclusion domain added to an endopeptidase framework creates the machine for activation of granular serine proteases
    • Turk D, Janji V, Stern I, Podobnik M, Lamba D, Weis Dahl S, Lauritzen C, Pedersen J, Turk V, Turk B. Structure of human dipeptidyl peptidase I (cathepsin C): exclusion domain added to an endopeptidase framework creates the machine for activation of granular serine proteases. EMBO J. 2001; 20: 6570-6582.
    • (2001) EMBO J , vol.20 , pp. 6570-6582
    • Turk, D.1    Janji, V.2    Stern, I.3    Podobnik, M.4    Lamba, D.5    Weis Dahl, S.6    Lauritzen, C.7    Pedersen, J.8    Turk, V.9    Turk, B.10
  • 21
    • 57849091626 scopus 로고    scopus 로고
    • Morris GM, Goodsell DS, Huey R, Hart WE, Halliday RS, Belew RK, Olson AJ. AutoDock version 3.05
    • Morris GM, Goodsell DS, Huey R, Hart WE, Halliday RS, Belew RK, Olson AJ. AutoDock (version 3.05).
  • 23
    • 84986492477 scopus 로고
    • Atomic charges derived from semiempirical methods
    • Besler BH, Merz KM Jr, Kollman PA. Atomic charges derived from semiempirical methods. J. Comput. Chem. 1990; 11: 431-439.
    • (1990) J. Comput. Chem , vol.11 , pp. 431-439
    • Besler, B.H.1    Merz Jr, K.M.2    Kollman, P.A.3
  • 24
    • 57849135421 scopus 로고    scopus 로고
    • Goddard TD, Kneller DG. SPARKY 3. University of California: San Francisco.
    • Goddard TD, Kneller DG. SPARKY 3. University of California: San Francisco.
  • 26
    • 77956993474 scopus 로고
    • Preparation and specificity of dipeptidyl peptidase I
    • McDonald JK, Callahan PX, Ellis P. Preparation and specificity of dipeptidyl peptidase I. Methods Ezymol. 1971; 25B: 272-281.
    • (1971) Methods Ezymol , vol.25 B , pp. 272-281
    • McDonald, J.K.1    Callahan, P.X.2    Ellis, P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.