Synthesis of a TMC-95A ketomethylene analogue by cyclization via intramolecular Suzuki coupling

被引：51

作者：

Kaiser, M

Siciliano, C

Assfalg-Machleidt, I

Groll, M

Milbradt, AG

Moroder, L ^{[1
]}

机构：

[1] AG Bioorgan Chem, Max Planck Inst Biochem, D-82152 Martinsried, Germany

[2] Univ Munich, Adolf Butenandt Inst, D-80336 Munich, Germany

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 19期

关键词：

D O I：

10.1021/ol035178f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A TMC-95A analogue extended at the C-terminus with NlePsi[COCH2]Gly-Ala-Ala-NH2 Was synthesized via side-chain cyclization of the linear precursor by a Suzuki cross-coupling reaction in solution to analyze the effect of additional P' residues on the inhibitory potency against yeast proteasome.

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页码：3435 / 3437

页数：3

相关论文

共 31 条

[1] A concise formal total synthesis of TMC-95A/B proteasome inhibitors [J].

Albrecht, BK ;

Williams, RM .

ORGANIC LETTERS, 2003, 5 (02) :197-200

[2]

[Anonymous], 2003, ANGEW CHEM, V115, P2758

[3] The proteasome [J].

Bochtler, M ;

Ditzel, L ;

Groll, M ;

Hartmann, C ;

Huber, R .

ANNUAL REVIEW OF BIOPHYSICS AND BIOMOLECULAR STRUCTURE, 1999, 28 :295-+

[4] Structure and functions of the 20S and 26S proteasomes [J].

Coux, O ;

Tanaka, K ;

Goldberg, AL .

ANNUAL REVIEW OF BIOCHEMISTRY, 1996, 65 :801-847

[5] Two syntheses of the 16- and 17-membered DEF ring systems of chloropeptin and complestatin [J].

Elder, AM ;

Rich, DH .

ORGANIC LETTERS, 1999, 1 (09) :1443-1446

[6] Crystal structure of epoxomicin:20S proteasome reveals a molecular basis for selectivity of α′,β′-epoxyketone proteasome inhibitors [J].

Groll, M ;

Kim, KB ;

Kairies, N ;

Huber, R ;

Crews, CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) :1237-1238

[7] Structure of 20S proteasome from yeast at 2.4 angstrom resolution [J].

Groll, M ;

Ditzel, L ;

Lowe, J ;

Stock, D ;

Bochtler, M ;

Bartunik, HD ;

Huber, R .

NATURE, 1997, 386 (6624) :463-471

[8] Crystal structure of the 20 S proteasome: TMC-95A complex: A non-covalent proteasome inhibitor [J].

Groll, M ;

Koguchi, Y ;

Huber, R ;

Kohno, J .

JOURNAL OF MOLECULAR BIOLOGY, 2001, 311 (03) :543-548

[9] The ubiquitin system [J].

Hershko, A ;

Ciechanover, A .

ANNUAL REVIEW OF BIOCHEMISTRY, 1998, 67 :425-479

[10] Total synthesis of TMC-95A [J].

Inoue, M ;

Sakazaki, H ;

Furuyama, H ;

Hirama, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (23) :2654-2657

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