Argifin; efficient solid phase total synthesis and evalution of analogues of acyclic peptide

被引:15
作者
Sunazuka, Toshiaki [1 ]
Sugawara, Akihiro [1 ]
Iguchi, Kanami [1 ]
Hirose, Tomoyasu [1 ]
Nagai, Kenichiro [1 ]
Noguchi, Yoshihiko [1 ]
Saito, Yoshifumi [1 ]
Yamamoto, Tsuyoshi [1 ]
Ui, Hideaki [1 ]
Gouda, Hiroaki [2 ]
Shiomi, Kazuro [1 ]
Watanabe, Takeshi [3 ]
Omura, Satoshi [1 ]
机构
[1] Kitasato Univ, Grad Sch Infect Control Sci, Kitasato Inst Life Sci, Minato Ku, Tokyo 1088641, Japan
[2] Kitasato Univ, Sch Pharmaceut Sci, Minato Ku, Tokyo 1088641, Japan
[3] Niigata Univ, Fac Agr, Dept Appl Biol Chem, Niigata 9502181, Japan
关键词
Argifin; Chitinase; Solid phase; Serratia marcescens; GLIOCLADIUM SP FTD-0668; CHITINASE INHIBITOR;
D O I
10.1016/j.bmc.2009.02.047
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
An effective solid phase synthesis of Argifin, providing subsequent access to effective synthesis of analogues, was developed in 13% overall yield, as well as elucidating structure-activity relationships. The novel acyclic peptide 18b, prepared from a synthetic intermediate of Argifin, was found to be 70 times more potent as an inhibitor of Serratia marcescens chitinases B than Argifin itself (c) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2751 / 2758
页数:8
相关论文
共 19 条
[1]   Structure-based dissection of the natural product cyclopentapeptide chitinase inhibitor argifin [J].
Andersen, Ole A. ;
Nathubhai, Amit ;
Dixon, Mark J. ;
Eggleston, Ian M. ;
van Aalten, Daan M. F. .
CHEMISTRY & BIOLOGY, 2008, 15 (03) :295-301
[2]   Argifin, a new chitinase inhibitor, produced by Gliocladium sp FTD-0668 -: II.: Isolation, physico-chemical properties, and structure elucidation [J].
Arai, N ;
Shiomi, K ;
Iwai, Y ;
Omura, S .
JOURNAL OF ANTIBIOTICS, 2000, 53 (06) :609-614
[3]   CHITINASE-B FROM SERRATIA-MARCESCENS-BJL200 IS EXPORTED TO THE PERIPLASM WITHOUT PROCESSING [J].
BRURBERG, MB ;
EIJSINK, VGH ;
HAANDRIKMAN, AJ ;
VENEMA, G ;
NES, IF .
MICROBIOLOGY-SGM, 1995, 141 :123-131
[4]   A NOVEL LYSINE-PROTECTING PROCEDURE FOR CONTINUOUS-FLOW SOLID-PHASE SYNTHESIS OF BRANCHED PEPTIDES [J].
BYCROFT, BW ;
CHAN, WC ;
CHHABRA, SR ;
HONE, ND .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (09) :778-779
[5]   CHITINASE AND CHITIN SYNTHASE .1. COUNTERBALANCING ACTIVITIES IN CELL-SEPARATION OF SACCHAROMYCES-CEREVISIAE [J].
CABIB, E ;
SILVERMAN, SJ ;
SHAW, JA .
JOURNAL OF GENERAL MICROBIOLOGY, 1992, 138 :97-102
[6]   An appraisal of new variants of Dde amine protecting group for solid phase peptide synthesis [J].
Chhabra, SR ;
Hothi, B ;
Evans, DJ ;
White, PD ;
Bycroft, BW ;
Chan, WC .
TETRAHEDRON LETTERS, 1998, 39 (12) :1603-1606
[7]   An efficient synthesis of argifin: A natural product chitinase inhibitor with chemotherapeutic potential [J].
Dixon, MJ ;
Andersen, OA ;
van Aalten, DMF ;
Eggleston, IM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (21) :4717-4721
[8]  
HIROSE T, J ANTIBIOT UNPUB
[9]   The X-ray structure of a chitinase from the pathogenic fungus Coccidioides immitis [J].
Hollis, T ;
Monzingo, AF ;
Bortone, K ;
Ernst, S ;
Cox, R ;
Robertus, JD .
PROTEIN SCIENCE, 2000, 9 (03) :544-551
[10]   High-resolution structures of a chitinase complexed with natural product cyclopentapeptide inhibitors: Mimicry of carbohydrate substrate [J].
Houston, DR ;
Shiomi, K ;
Arai, N ;
Omura, S ;
Peter, MG ;
Turberg, A ;
Synstad, B ;
Eijsink, VGH ;
van Aalten, DMF .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (14) :9127-9132