Biosynthesis of cyclopropane in natural products

2022 ◽  
Author(s):  
Suze Ma ◽  
Dhanaraju Mandalapu ◽  
Shu Wang ◽  
Qi Zhang
Keyword(s):  
Natural Products ◽  
Biochemical Properties ◽  
Structural Motif ◽  
Enzymatic Pathways

This review discusses the diverse enzymatic pathways in the biosynthesis of cyclopropane, a unique structural motif with important biochemical properties.

Total Synthesis of the Pseudoindoxyl Class of Natural Products

2021 ◽  
Author(s):  
Pawan Surendra Dhote ◽  
Pitambar Patel ◽  
Kumar Vanka ◽  
Chepuri Ramana
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Structural Motif ◽  
Large Set

The pseudoindoxyl sub-structural motif, amongst the large set of the indole class of alkaloids, represents a unique subset of the oxygenated indole class of the alkaloids family. A majority of...

Beyond conventional construction of phthalimide core: A review

2021 ◽  
Author(s):  
Suven Das
Keyword(s):  
Natural Products ◽  
Organic Materials ◽  
Structural Motif ◽  
Primary Amines ◽  
Common Strategy ◽  
Phthalic Acids

Phthalimides are privileged structural motif frequently found in natural products, pharmaceuticals and organic materials. The Most common strategy for their synthesis involves condensation of phthalic acids/anhydrides with primary amines. However,...

scholarly journals Biosynthesis of sulfonamide and sulfamate antibiotics in Actinomycete

2021 ◽  
Author(s):  
Takayoshi Awakawa ◽  
Lena Barra ◽  
Ikuro Abe
Keyword(s):  
Natural Products ◽  
Second Generation ◽  
Structural Motif ◽  
Organosulfur Compounds ◽  
Antibacterial Drugs ◽  
Structural Motifs ◽  
Detailed Understanding ◽  
Bacterial Genus ◽  
Current State ◽  
Biosynthetic Engineering

Abstract Sulfonamides and sulfamates are a group of organosulfur compounds that contain the signature sulfamoyl structural motif. These compounds were initially only known as synthetic antibacterial drugs but were later also discovered as natural products. Eight highly potent examples have been isolated from actinomycetes to date, illustrating the large biosynthetic repertoire of this bacterial genus. For the biosynthesis of these compounds, several distinct and unique biosynthetic machineries have been discovered, capable to generate the unique S-N bond. For the creation of novel, second generation natural products by biosynthetic engineering efforts, a detailed understanding of the underlying enzyme machinery towards potent structural motifs is crucial. In this review, we aim to summarize the current state of knowledge on sulfonamide and sulfamate biosynthesis. A detailed discussion for the secondary sulfamate ascamycin, the tertiary sulfonamide sulfadixiamycin A, and the secondary sulfonamide SB-203208 is provided and their bioactivities and mode of actions are discussed.

scholarly journals Bioinspired Syntheses of Herqulines B and C from Cyclodipeptide Mycocyclosin

2018 ◽  
Author(s):  
Xu Zhu ◽  
Christopher C. McAtee ◽  
Corinna Schindler
Keyword(s):  
Natural Products ◽  
Oxidation State ◽  
Structural Motif ◽  
Hypervalent Iodine ◽  
Birch Reduction ◽  
System Characteristic

<div>A bioinspired approach for the syntheses of herqulines B and C is reported that takes advantage of an Ltyrosine-derived diketopiperazine, a mycocyclosin analog, as a synthetic precursor. The strategy relies on a series of consecutive reductions to adjust the mycocyclosin oxidation state to that observed in the herquline class of natural products. The strained and distorted L-tyrosine-based biaryl system characteristic for mycocyclosin is selectively converted to the 1,4-diketone structural motif common to the herqulines via initial hypervalent iodine-mediated dearomatization and a subsequent directed Birch reduction, enabled by an intramolecular H-source. The piperazine oxidation state is accessible in an iron-catalyzed reduction of the diketopiperazine precursor.</div>

scholarly journals A General Approach to 2,2-Disubstituted Indoxyls: Total Synthesis of Brevianamide A and Trigonoliimine C

2021 ◽  
Author(s):  
Fan Xu ◽  
Myles Smith
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Bioactive Compounds ◽  
Structural Motif ◽  
Total Syntheses ◽  
Broad Scope ◽  
Nucleophilic Trapping ◽  
General Method

The indoxyl unit is a common structural motif in alkaloid natural products and bioactive compounds. Here, we report a general method that transforms readily available 2-substituted indoles into 2,2-disubstituted indoxyls via nucleophile coupling with a 2-alkoxyindoxyl intermediate and showcase its utility in short total syntheses of the alkaloids brevianamide A (7 steps) and trigonoliimine C (6 steps). The developed method is operationally simple and demonstrates broad scope in terms of nucleophile identity and indole substitution, tolerating 2-alkyl substituents and free indole N–H groups, elements beyond the scope of most prior approaches. Spirocyclic indoxyl products are also accessible via intramolecular nucleophilic trapping.

scholarly journals Bioinspired Syntheses of Herqulines B and C from Cyclodipeptide Mycocyclosin

2018 ◽  
Author(s):  
Xu Zhu ◽  
Christopher C. McAtee ◽  
Corinna Schindler
Keyword(s):  
Natural Products ◽  
Oxidation State ◽  
Structural Motif ◽  
Hypervalent Iodine ◽  
Birch Reduction ◽  
System Characteristic

<div>A bioinspired approach for the syntheses of herqulines B and C is reported that takes advantage of an Ltyrosine-derived diketopiperazine, a mycocyclosin analog, as a synthetic precursor. The strategy relies on a series of consecutive reductions to adjust the mycocyclosin oxidation state to that observed in the herquline class of natural products. The strained and distorted L-tyrosine-based biaryl system characteristic for mycocyclosin is selectively converted to the 1,4-diketone structural motif common to the herqulines via initial hypervalent iodine-mediated dearomatization and a subsequent directed Birch reduction, enabled by an intramolecular H-source. The piperazine oxidation state is accessible in an iron-catalyzed reduction of the diketopiperazine precursor.</div>

Synthetic Approaches to 2,6-trans-Tetrahydropyrans

Synthesis ◽  
2017 ◽  
Vol 49 (22) ◽  
pp. 4899-4916 ◽  
Author(s):  
Rongbiao Tong ◽  
Zhihong Zhang
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Michael Addition ◽  
Synthetic Methods ◽  
Bioactive Molecules ◽  
Structural Motif ◽  
Heck Cyclization ◽  
Epoxide Opening ◽  
Oxocarbenium Ion ◽  
Synthetic Approaches

Being different from 2,6-cis-tetrahydropyrans (2,6-cis-THPs), the corresponding 2,6-trans-THPs are thermodynamically less stable and more challenging to construct. The fact that there are many natural products and/or bioactive molecules containing this 2,6-trans-THP subunit has led to the development of many efficient synthetic approaches to access 2,6-trans-THPs. This review summarizes various synthetic methods reported for this structural motif and/or related applications in the total synthesis of natural products.1 Introduction2 Nucleophilic Addition to an Oxocarbenium Ion (Strategy A)3 Intramolecular Oxa-Michael Addition (Strategy B)4 Intermolecular Michael Addition to Dihydropyranones (Strategy A)5 The Heck–Matsuda (Strategy A) Reaction and Oxa-Heck Cyclization (Strategy B)6 Intramolecular SN2 Substitution and Epoxide Opening (Strategy B)7 Miscellaneous Methods8 Conclusion and Outlook

scholarly journals Tumor-associated mutations in a conserved structural motif alter physical and biochemical properties of human RAD51 recombinase

2014 ◽  
Vol 43 (2) ◽  
pp. 1098-1111 ◽  
Author(s):  
Jianhong Chen ◽  
Milagros D. Morrical ◽  
Katherine A. Donigan ◽  
Joanne B. Weidhaas ◽  
Joann B. Sweasy ◽  
...  
Keyword(s):  
Biochemical Properties ◽  
Structural Motif ◽  
Human Rad51

scholarly journals Sex-specific triacylglycerides are widely conserved in Drosophila and mediate mating behavior

eLife ◽  
2014 ◽  
Vol 3 ◽  
Author(s):  
Jacqueline SR Chin ◽  
Shane R Ellis ◽  
Huong T Pham ◽  
Stephen J Blanksby ◽  
Kenji Mori ◽  
...  
Keyword(s):  
Natural Products ◽  
Chemical Cues ◽  
Fatty Acyl ◽  
Structural Motif ◽  
Insect Pheromones ◽  
Tiglic Acid ◽  
Oxygen Groups ◽  
And Function ◽  
Specialized Diet ◽  
Ejaculatory Bulb

Pheromones play an important role in the behavior, ecology, and evolution of many organisms. The structure of many insect pheromones typically consists of a hydrocarbon backbone, occasionally modified with various functional oxygen groups. Here we show that sex-specific triacylclyerides (TAGs) are broadly conserved across the subgenus Drosophila in 11 species and represent a novel class of pheromones that has been largely overlooked. In desert-adapted drosophilids, 13 different TAGs are secreted exclusively by males from the ejaculatory bulb, transferred to females during mating, and function synergistically to inhibit courtship from other males. Sex-specific TAGs are comprised of at least one short branched tiglic acid and a long linear fatty acyl component, an unusual structural motif that has not been reported before in other natural products. The diversification of chemical cues used by desert-adapted Drosophila as pheromones may be related to their specialized diet of fermenting cacti.

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