Synthesis of (2S,3R,4R)-Dihydroxyisoleucine for Use in Amatoxin Synthesis

被引：0

作者：

Chandra, Shambhu Deo ^{[1
]}

Gunasekera, Shanal ^{[1
]}

Noichl, Benjamin Philipp ^{[1
]}

Patrick, Brian O. ^{[1
]}

Perrin, David M. ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 17期

基金：

加拿大自然科学与工程研究理事会;

关键词：

MANNICH-TYPE REACTIONS; RNA-POLYMERASE-II; ALPHA-AMANITIN; STRUCTURAL BASIS; TRANSCRIPTION; ACID; OXAZABOROLIDINES; INHIBITION; MECHANISM; PEPTIDES;

D O I：

10.1021/acs.joc.4c01051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a streamlined synthesis of (2S,3R,4R)-4,5-dihydroxy isoleucine (DHIle), an amino acid found in alpha-amanitin, which appears to be critical for toxicity. This synthetic route is transition metal-free and enables the production of significant quantities of DHIle with suitable protection for use in peptide synthesis. Its incorporation into a cytotoxic amatoxin analog is reported.

引用

页码：12739 / 12747

页数：9

共 48 条

[21] Cryo-EM structure of a mammalian RNA polymerase II elongation complex inhibited by -amanitin
Liu, Xiangyang
Farnung, Lucas
Wigge, Christoph
Cramer, Patrick
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2018, 293 (19) : 7189 - 7194
[22] OXAZABOROLIDINES AND DIOXABOROLIDINES IN ENANTIOSELECTIVE CATALYSIS
LOHRAY, BB
BHUSHAN, V
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (06): : 729 - 730
[23] Total Synthesis of α- and β-Amanitin
Lutz, Christian
Simon, Werner
Werner-Simon, Susanne
Pahl, Andreas
Mueller, Christoph
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (28) : 11390 - 11393
[24] A Practical and Efficient Total Synthesis of Potent Insulinotropic (2S,3R,4S)-4-Hydroxyisoleucine through a Chiral N-Protected γ-Keto-α-aminoester
Marin, Sandra De Lamo
Catala, Cedric
Kumar, Sreekantha Ratna
Valleix, Alain
Wagner, Alain
Mioskowski, Charles
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (21) : 3985 - 3989
[25] Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates
Matinkhoo, Kaveh
Wong, Antonio A. W. L.
Hambira, Chido M.
Kato, Brandon
Wei, Charlie
Mueller, Christoph
Hechler, Torsten
Braun, Alexandra
Gallo, Francesca
Pahl, Andreas
Perrin, David M.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (40) : 10282 - 10292
[26] Synthesis of the Death-Cap Mushroom Toxin α-Amanitin
Matinkhoo, Kaveh
Pryyma, Alla
Todorovic, Mihajlo
Patrick, Brian O.
Perrin, David M.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (21) : 6513 - 6517
[27] Direct asymmetric anti-Mannich-Type reactions catalyzed by a designed amino acid
Mitsumori, S
Zhang, H
Cheong, PHY
Houk, KN
Tanaka, F
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) : 1040 - 1041
[28] Therapeutic Potential of Amanitin-Conjugated Anti-Epithelial Cell Adhesion Molecule Monoclonal Antibody Against Pancreatic Carcinoma
Moldenhauer, Gerhard
Salnikov, Alexei V.
Luettgau, Sandra
Herr, Ingrid
Anderl, Jan
Faulstich, Heinz
[J]. JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 2012, 104 (08): : 622 - 634
[29] Effective production of amanitins by two-step cultivation of the basidiomycete, Galerina fasciculata GF-060
Muraoka, S
Shinozawa, T
[J]. JOURNAL OF BIOSCIENCE AND BIOENGINEERING, 2000, 89 (01) : 73 - 76
[30] The scope of the direct proline-catalyzed asymmetric addition of ketones to imines
Notz, W
Watanabe, S
Chowdari, NS
Zhong, GF
Betancort, JM
Tanaka, F
Barbas, CF
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1131 - 1140

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