81644-19-1

Basic information

• Product Name: 10-deoxymethynolide
• Synonyms: 10-deoxymethynolide
• CAS NO: 81644-19-1
• Molecular Formula: C17H28O4
• Molecular Weight: 296.40182
• Mol File: 81644-19-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 460.7°Cat760mmHg
• Flash Point: 161.3°C
• Appearance: /
• Density: 0.972g/cm³
• Vapor Pressure: 2.01E-10mmHg at 25°C
• Refractive Index: 1.45
• CAS DataBase Reference: 10-deoxymethynolide(CAS DataBase Reference)
• NIST Chemistry Reference: 10-deoxymethynolide(81644-19-1)
• EPA Substance Registry System: 10-deoxymethynolide(81644-19-1)

Safety Data

• Hazardous Substances Data: 81644-19-1(Hazardous Substances Data)

Usage

Description

10-Deoxymethynolide is a macrolide compound characterized by its unique structure, consisting of oxacyclododec-9-ene-2,8-dione with four methyl substituents at positions 3, 5, 7, and 11, a hydroxy group at position 4, and an ethyl substituent at position 12. It is the aglycone of the macrolide antibiotic 10-deoxymethynolide, which has potential applications in various industries due to its unique properties.

Uses

Used in Pharmaceutical Industry:
10-Deoxymethynolide is used as a pharmaceutical compound for its potential antibiotic properties. Its unique structure allows it to target specific bacterial cells, making it a promising candidate for the development of new antibiotics to combat drug-resistant infections.
Used in Drug Development:
10-Deoxymethynolide is used as a starting point for drug development in the pharmaceutical industry. Its unique structure and properties can be further modified and optimized to create new drugs with improved efficacy and reduced side effects.
Used in Chemical Research:
10-Deoxymethynolide is used as a research compound in chemical research to study its properties and potential applications. Its unique structure and functional groups make it an interesting subject for investigation, which can lead to the discovery of new chemical reactions and applications.
Used in Cosmetics Industry:
10-Deoxymethynolide can be used as an active ingredient in cosmetics for its potential antimicrobial and anti-inflammatory properties. Its ability to target specific cells and modulate biological pathways can make it a valuable component in skincare products and other cosmetic formulations.
Used in Agricultural Industry:
10-Deoxymethynolide can be used as a biopesticide in the agricultural industry to control pests and diseases affecting crops. Its unique structure and properties can be harnessed to develop new and effective pest control solutions that are environmentally friendly and safe for use.

InChI:InChI=1/C17H28O4/c1-6-15-10(2)7-8-14(18)11(3)9-12(4)16(19)13(5)17(20)21-15/h7-8,10-13,15-16,19H,6,9H2,1-5H3/b8-7+/t10-,11-,12+,13-,15-,16+/m1/s1

Upstream product

• 1141775-93-0 tert-butyldimethyl(((3R,4R)-4-methylhex-5-en-3-yl)oxy)silane 
• 114181-55-4 (2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal 
• 78433-59-7 (2R,3R)-3-<(tert-butyldimethylsilyl)oxy>-2-methylpentan-1-ol 
• 1448017-63-7 C₁₇H₃₆O₂Si 

Downstream Products

• 1583315-19-8 ((3R,4S,5S,7R,11R,12R,E)-12-ethyl-3,5,7,11-tetramethyl-2,8-dioxo-1-oxacyclododec-9-en-4-yl) 2-((dimethylamino)methyl)benzoate 
• 1583315-29-0 C₂₇H₃₉NO₆ 
• 1583315-21-2 ((3R,4S,5S,7R,11R,12R,E)-12-ethyl-3,5,7,11-tetramethyl-2,8-dioxo-1-oxacyclododec-9-en-4-yl) 3-((dimethylamino)methyl)benzoate 
• 1583315-20-1 ((3R,4S,5S,7R,11R,12R,E)-12-ethyl-3,5,7,11-tetramethyl-2,8-dioxo-1-oxacyclododec-9-en-4-yl) 4-((dimethylamino)methyl)benzoate 
• 36826-66-1 YC-17 

Relevant articles and documents

A Single Active Site Mutation in the Pikromycin Thioesterase Generates a More Effective Macrocyclization Catalyst

Macrolactonization of natural product analogs presents a significant challenge to both biosynthetic assembly and synthetic chemistry. In the preceding paper, we identified a thioesterase (TE) domain catalytic bottleneck processing unnatural substrates in the pikromycin (Pik) system, preventing the formation of epimerized macrolactones. Here, we perform molecular dynamics simulations showing the epimerized hexaketide was accommodated within the Pik TE active site; however, intrinsic conformational preferences of the substrate resulted in predominately unproductive conformations, in agreement with the observed hydrolysis. Accordingly, we engineered the stereoselective Pik TE to yield a variant (TES148C) with improved reaction kinetics and gain-of-function processing of an unnatural, epimerized hexaketide. Quantum mechanical comparison of model TES148C and TEWT reaction coordinate diagrams revealed a change in mechanism from a stepwise addition-elimination (TEWT) to a lower energy concerted acyl substitution (TES148C), accounting for the gain-of-function and improved reaction kinetics. Finally, we introduced the S148C mutation into a polyketide synthase module (PikAIII-TE) to impart increased substrate flexibility, enabling the production of diastereomeric macrolactones.

Engineering the Substrate Specificity of a Modular Polyketide Synthase for Installation of Consecutive Non-Natural Extender Units

There is significant interest in diversifying the structures of polyketides to create new analogues of these bioactive molecules. This has traditionally been done by focusing on engineering the acyltransferase (AT) domains of polyketide synthases (PKSs) responsible for the incorporation of malonyl-CoA extender units. Non-natural extender units have been utilized by engineered PKSs previously; however, most of the work to date has been accomplished with ATs that are either naturally promiscuous and/or located in terminal modules lacking downstream bottlenecks. These limitations have prevented the engineering of ATs with low native promiscuity and the study of any potential gatekeeping effects by domains downstream of an engineered AT. In an effort to address this gap in PKS engineering knowledge, the substrate preferences of the final two modules of the pikromycin PKS were compared for several non-natural extender units and through active site mutagenesis. This led to engineering of the methylmalonyl-CoA specificity of both modules and inversion of their selectivity to prefer consecutive non-natural derivatives. Analysis of the product distributions of these bimodular reactions revealed unexpected metabolites resulting from gatekeeping by the downstream ketoreductase and ketosynthase domains. Despite these new bottlenecks, AT engineering provided the first full-length polyketide products incorporating two non-natural extender units. Together, this combination of tandem AT engineering and the identification of previously poorly characterized bottlenecks provides a platform for future advancements in the field.

Biocatalytic synthesis of pikromycin, methymycin, neomethymycin, novamethymycin, and ketomethymycin

A biocatalytic platform that employs the final two monomodular type I polyketide synthases of the pikromycin pathway in vitro followed by direct appendage of d-desosamine and final C-H oxidation(s) in vivo was developed and applied toward the synthesis of a suite of 12- and 14-membered ring macrolide natural products. This methodology delivered both compound classes in 13 steps (longest linear sequence) from commercially available (R)-Roche ester in >10% overall yields.