Direct Biomimetic Synthesis of β-Carboline Alkaloids from Two Amino Acids

被引：30

作者：

Wang, Zi-Xuan ^{[1
]}

Xiang, Jia-Chen ^{[1
]}

Cheng, Yan ^{[1
]}

Ma, Jin-Tian ^{[1
]}

Wu, Yan-Dong ^{[1
]}

Wu, An-Xin ^{[1
]}

机构：

[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

基金：

中国国家自然科学基金;

关键词：

TUNICATE EUDISTOMA-OLIVACEUM; ASSISTED SYNTHESIS; ORGANIC-SYNTHESIS; ANTITUMOR AGENTS; NATURAL-PRODUCTS; METHYL KETONES; ANTI-HIV; DERIVATIVES; REAGENT; ALPHA;

D O I：

10.1021/acs.joc.8b01668

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The increasing importance of enzyme mimics in organic synthesis inspired us to design a novel biomimetic synthesis of beta-carboline alkaloids directly from tryptophan and a second amino acid. This novel one-pot protocol utilizes abundant and readily available starting materials and thus presents a green and user-friendly alternative to conventional methods that rely on stepwise synthesis. Driven by molecular iodine and TFA, decarboxylation, deamination, Pictet-Spengler reaction, and oxidation reactions proceeded sequentially, transforming biomass amino acids into value-added alkaloid motifs.

引用

收藏

页码：12247 / 12254

页数：8

相关论文

共 62 条

[1] BROMINATED BETA-CARBOLINES FROM THE MARINE TUNICATE EUDISTOMA-ALBUM [J].

ADESANYA, SA ;

CHBANI, M ;

PAIS, M ;

DEBITUS, C .

JOURNAL OF NATURAL PRODUCTS, 1992, 55 (04) :525-527

[2] Catalytic conversion of nitrogen to ammonia by an iron model complex [J].

Anderson, John S. ;

Rittle, Jonathan ;

Peters, Jonas C. .

NATURE, 2013, 501 (7465) :84-+

[3] Catalytic Reduction of Dinitrogen to Ammonia by Use of Molybdenum-Nitride Complexes Bearing a Tridentate Triphosphine as Catalysts [J].

Arashiba, Kazuya ;

Kinoshita, Eriko ;

Kuriyama, Shogo ;

Eizawa, Aya ;

Nakajima, Kazunari ;

Tanaka, Hiromasa ;

Yoshizawa, Kazunari ;

Nishibayashi, Yoshiaki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (17) :5666-5669

[4] An iron-iron hydrogenase mimic with appended electron reservoir for efficient proton reduction in aqueous media [J].

Becker, Rene ;

Amirjalayer, Saeed ;

Li, Ping ;

Woutersen, Sander ;

Reek, Joost N. H. .

SCIENCE ADVANCES, 2016, 2 (01)

[5] MIMICS OF TRANSAMINASE ENZYMES [J].

BRESLOW, R ;

CZARNIK, AW ;

LAUER, M ;

LEPPKES, R ;

WINKLER, J ;

ZIMMERMAN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :1969-1979

[6] A β-carboline alkaloid from the soft coral Lignopsis spongiosum [J].

Cabrera, GM ;

Seldes, AM .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (05) :759-760

[7] Five New β-Carboline-Type Alkaloids from Stellaria dichotoma var. lanceolata [J].

Cao, Li-Hua ;

Zhang, Wei ;

Luo, Jian-Guang ;

Kong, Ling-Yi .

HELVETICA CHIMICA ACTA, 2012, 95 (06) :1018-1025

[8] β-Carboline alkaloids:: Biochemical and pharmacological functions [J].

Cao, Rihui ;

Peng, Wenlie ;

Wang, Zihou ;

Xu, Anlong .

CURRENT MEDICINAL CHEMISTRY, 2007, 14 (04) :479-500

[9] Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction [J].

Chen, Jianfeng ;

Gong, Xing ;

Li, Jianyu ;

Li, Yingkun ;

Ma, Jiguo ;

Hou, Chengkang ;

Zhao, Guoqing ;

Yuan, Weicheng ;

Zhao, Baoguo .

SCIENCE, 2018, 360 (6396) :1438-+

[10] Discovery of McbB, an Enzyme Catalyzing the β-Carboline Skeleton Construction in the Marinacarboline Biosynthetic Pathway [J].

Chen, Qi ;

Ji, Changtao ;

Song, Yongxiang ;

Huang, Hongbo ;

Ma, Junying ;

Tian, Xinpeng ;

Ju, Jianhua .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) :9980-9984

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