Syntheses of 2-[(1<i>S</i>,3<i>S</i>)-1-Amino-3-carboxy-3-hydroxypropyl]thiazole-4-carboxylic Acid and the Tripeptide Skeleton of Nosiheptide Containing the Acid

Shin, Chung‐gi; Nakamura, Yutaka; Yamada, Yasuhiro; Yonezawa, Yasuchika; Umemura, Kazuyuki; Yoshimura, Juji

doi:10.1246/bcsj.68.3151

Cited by 25 publications

(17 citation statements)

References 7 publications

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“…Unsurprisingly, the Hantzsch reaction has found wide use in the synthesis of thiopeptide thiazole fragments. Examples include the thiazole building blocks of promothiocin A ( 3 ),44 amythiamicin D ( 4 ),24 GE2270A ( 5 ),48–50 nosiheptide ( 6 ),51, 52 A10255G,39 thiocilline,53 and cyclothiazomycin 54…”

Section: Building Blocks Of Thiopeptide Antibioticsmentioning

confidence: 99%

Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using Pt^II Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity

Cavarzan

Bianchini

Sgarbossa

et al. 2009

Chemistry A European J

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The enantioselective Baeyer-Villiger oxidation of cyclic ketones is a challenging reaction, especially when using environmentally friendly oxidants. The reaction was carried out in water by using soft Lewis acid Pt(II) complexes that have chiral diphosphines as well as monophosphines. Addition of a surfactant is crucial, which leads to the formation of micelles that act as nanoreactors in which the substrate and catalyst encounter each other in an ordered medium that in several cases positively influences both the conversion and the selectivity of the reactions. This is due to the combination of the hydrophobic effect (which confines the components of the reaction in the micelles), together with supramolecular interactions between the partners within the ordered palisade provided by the alkyl chains of the surfactant. For the oxidation of meso-cyclobutanones, addition of surfactant allowed the reaction to proceed in high yields and the enantiometic excess (ee; 56%) was higher than in organic solvents. Subsequent extension to meso-cyclohexanones resulted in a general decrease in yields but an enhancement of enantioselectivity (ee up to 92%) moving from organic to water-surfactant media, regardless of the substrate or the catalyst employed. Different behaviour was observed with chiral cyclobutanones 7 and 10: with 7 the best catalyst was 1 g, whereas with the larger substrate, 10, complexes 1 a-b performed better in terms of enantioselectivity. Each combination of substrate, catalyst and surfactant is a new system and supramolecular reciprocal interactions together with the hydrophobic character of the counterparts play crucial roles. The asymmetric Baeyer-Villiger oxidation in water catalyzed by 1 a-h in the presence of micelles is a viable reaction that often benefits from the hydrophobic effect, leading to substantial increases in enantioselectivity.

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Section: Building Blocks Of Thiopeptide Antibioticsmentioning

confidence: 99%

Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using Pt^II Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity

Cavarzan

Bianchini

Sgarbossa

et al. 2009

Chemistry A European J

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“…Examples include the thiazole building blocks of promothiocin A (3), [44] amythiamicin D (4), [24] GE2270A (5), [48][49][50] nosiheptide (6), [51,52] A10255G, [39] thiocilline, [53] and cyclothiazomycin. [54] By analogy with the use of serine derivatives in the synthesis of oxazolines, and hence oxazoles, the biomimetic cyclodehydration of the corresponding cysteine derivatives 26 would be expected to give thiazolines 27 and hence thiazoles 28.…”

Section: Thiazolesmentioning

confidence: 99%

From Amino Acids to Heteroaromatics—Thiopeptide Antibiotics, Nature's Heterocyclic Peptides

2007

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Amino acids, the building blocks of proteins, also serve as precursors to a wide range of other naturally occurring substances including alkaloids, antibiotics, and, the subject of this Review, heterocyclic peptides. Simple alpha-amino acids are converted into complex arrays of heteroaromatic rings that display interesting and potent biological activity. The thiopeptide antibiotics, with their complex molecular architectures, are wonderful examples. In this Review we show how organic chemists have developed innovative methods for the synthesis of the heterocyclic ring systems, including routes inspired by the likely biosynthetic processes, and successfully assembled such building blocks into the final target molecule by application of orthogonal protecting groups and coupling methodologies.

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“…Erwartungsgemäß fand die Hantzsch‐Reaktion breite Verwendung für die Synthese von Thiazolfragmenten von Thiopeptiden. Beispiele sind die Synthesen der Thiazolbausteine von Promothiocin A ( 3 ),44 Amythiamicin D ( 4 ),24 GE2270A ( 5 ),48–50 Nosiheptid ( 6 ),51, 52 A10255G,39 Thiocillin53 und Cyclothiazomycin 54…”

Section: Bausteine Für Thiopeptid‐antibiotikaunclassified

Von Aminosäuren zu Heteroarenen – Thiopeptid‐Antibiotika als heterocyclische Peptide aus der Natur

Hughes

Moody

2007

Angewandte Chemie

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Aminosäuren, die Bausteine der Proteine, sind zugleich auch Vorstufen für viele andere Naturstoffe wie Alkaloide, Antibiotika und, Thema dieses Aufsatzes, heterocyclische Peptide. Einfache α‐Aminosäuren werden dabei zu komplexen Anordnungen aus heteroaromatischen Ringen zusammengefügt, die sich ihrerseits durch interessante, hohe biologische Aktivität auszeichnen. Ein Beispiel dafür sind die Thiopeptid‐Antibiotika mit ihrer komplexen Molekülarchitektur. In diesem Aufsatz zeigen wir auf, wie Organiker innovative Methoden zur Synthese des heterocyclischen Ringsystems entwickelt haben, die teilweise auch durch die jeweiligen Biosyntheserouten inspiriert waren. Zielführend war dabei die geschickte Anwendung von orthogonalen Schutzgruppen und Kupplungsstrategien.

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Syntheses of 2-[(1S,3S)-1-Amino-3-carboxy-3-hydroxypropyl]thiazole-4-carboxylic Acid and the Tripeptide Skeleton of Nosiheptide Containing the Acid

Cited by 25 publications

References 7 publications

Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using Pt^II Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity

Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using Pt^II Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity

From Amino Acids to Heteroaromatics—Thiopeptide Antibiotics, Nature's Heterocyclic Peptides

Von Aminosäuren zu Heteroarenen – Thiopeptid‐Antibiotika als heterocyclische Peptide aus der Natur

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Syntheses of 2-[(1S,3S)-1-Amino-3-carboxy-3-hydroxypropyl]thiazole-4-carboxylic Acid and the Tripeptide Skeleton of Nosiheptide Containing the Acid

Cited by 25 publications

References 7 publications

Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using PtII Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity

Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using PtII Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity

From Amino Acids to Heteroaromatics—Thiopeptide Antibiotics, Nature's Heterocyclic Peptides

Von Aminosäuren zu Heteroarenen – Thiopeptid‐Antibiotika als heterocyclische Peptide aus der Natur

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Product

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Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using Pt^II Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity

Catalytic Asymmetric Baeyer–Villiger Oxidation in Water by Using Pt^II Catalysts and Hydrogen Peroxide: Supramolecular Control of Enantioselectivity