Piperazic acid-containing natural products: Isolation, biological relevance and total synthesis

被引：88

作者：

Oelke, Alexander J. ^{[1
,2
]}

France, David J. ^{[3
]}

Hofmann, Tatjana ^{[4
]}

Wuitschik, Georg ^{[5
]}

Ley, Steven V. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

[2] MIT, Dept Chem, Cambridge, MA 02139 USA

[3] Univ Glasgow, WestCHEM Sch Chem, Glasgow G12 8QQ, Lanark, Scotland

[4] Merck KGaA, Merck Serono Med Chem Darmstadt, D-64293 Darmstadt, Germany

[5] F Hoffmann La Roche Ltd, pRED, Therapeut Modal Synth & Proc Res, CH-4070 Basel, Switzerland

来源：

NATURAL PRODUCT REPORTS | 2011年 / 28卷 / 08期

基金：

英国工程与自然科学研究理事会;

关键词：

ANTITUMOR ANTIBIOTIC A83586C; STREPTOMYCES SP A92-308110; SEQUENCE-SPECIFIC BINDING; KEY SANDRAMYCIN ANALOGS; ANTI-TUMOR ANTIBIOTICS; HIGH OPTICAL PURITY; UNUSUAL AMINO-ACID; QUINOXAPEPTIN A-C; SANGLIFEHRIN-A; IMMUNOSUPPRESSANT SANGLIFEHRIN;

D O I：

10.1039/c1np00041a

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：

Since their first discovery in 1959, natural products containing the piperazic acid motif have been isolated from a variety of sources and exhibit diverse biological activity profiles. This review provides information about their isolation and biological activities, and presents an overview of recent total syntheses of these molecules.

引用

页码：1445 / 1471

页数：27

共 170 条

[1] Total synthesis and biological evaluation of tamandarin B analogues [J].

Adrio, Javier ;

Cuevas, Carmen ;

Manzanares, Ignacio ;

Joullie, Madeleine M. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5129-5138

[2] GE3, a novel hexadepsipeptide antitumor antibiotic produced by Streptomyces sp .2. Structure determination [J].

Agatsuma, T ;

Sakai, Y ;

Mizukami, T ;

Saitoh, Y .

JOURNAL OF ANTIBIOTICS, 1997, 50 (08) :704-708

[3] CRYSTAL AND MOLECULAR-STRUCTURE OF BBM-928-A, A NOVEL ANTI-TUMOR ANTIBIOTIC FROM ACTINOMADURA-LUZONENSIS [J].

ARNOLD, E ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (05) :1243-1244

[4] (S)-5-PYRROLIDIN-2-YL-1H-TETRAZOLE [J].

Aureggi, Valentina ;

Franckevicius, Vilius ;

Kitching, Matthew O. ;

Ley, Steven V. ;

Longbottom, Deborah A. ;

Oelke, Alexander J. ;

Sedelmeier, Gottfried .

ORGANIC SYNTHESES, 2008, 85 :72-+

[5] DNA recognition by quinoline antibiotics: Use of base-modified DNA molecules to investigate determinants of sequence-specific binding of luzopeptin. [J].

Bailly, C ;

Crow, S ;

Minnock, A ;

Waring, MJ .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2000, 19 (08) :1337-1353

[6] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].

BAL, BS ;

CHILDERS, WE ;

PINNICK, HW .

TETRAHEDRON, 1981, 37 (11) :2091-2096

[7] Recent developments in depsipeptide research [J].

Ballard, CE ;

Yu, H ;

Wang, B .

CURRENT MEDICINAL CHEMISTRY, 2002, 9 (04) :471-498

[8] Synthesis of derivatives of the novel cyclophilin-binding immunosuppressant sanglifehrin A with reduced numbers of polar functions [J].

Bänteli, R ;

Wagner, J ;

Zenke, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (12) :1609-1612

[9] A synthesis of the C1-N12 tripeptide fragment of sanglifehrin A [J].

Bänteli, R ;

Brun, I ;

Hall, P ;

Metternich, R .

TETRAHEDRON LETTERS, 1999, 40 (11) :2109-2112

[10] The binding mode of the DNA bisintercalator luzopeptin investigated using atomic force microscopy [J].

Berge, T ;

Haken, EL ;

Waring, MJ ;

Henderson, RM .

JOURNAL OF STRUCTURAL BIOLOGY, 2003, 142 (02) :241-246

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