74758-60-4

Basic information

• Product Name: protylonolide
• Synonyms: protylonolide;20-Deoxo-23-deoxytylonolide;23-Deoxy-20-deoxotylonolide;4-Desmethoxy-4,12,14β,16-tetramethyl-9-deoxy-9-oxo-6-des(2-oxoethyl)-6-ethylleuconolide;Tylactone
• CAS NO: 74758-60-4
• Molecular Formula: C₂₃H₃₈O₅
• Molecular Weight: 0
• Mol File: 74758-60-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 573.3°C at 760 mmHg
• Flash Point: 189.4°C
• Appearance: /
• Density: 0.982g/cm³
• Vapor Pressure: 1.58E-15mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: protylonolide(CAS DataBase Reference)
• NIST Chemistry Reference: protylonolide(74758-60-4)
• EPA Substance Registry System: protylonolide(74758-60-4)

Safety Data

• Hazardous Substances Data: 74758-60-4(Hazardous Substances Data)

Usage

Description

Protylonolide is a 16-membered macrolide that serves as the aglycone of the antibiotic 5-O-beta-D-mycaminosyltylactone.

Uses

Used in Pharmaceutical Industry:
Protylonolide is used as an antibiotic for its potential antimicrobial properties, contributing to the development of treatments for bacterial infections.

InChI:InChI=1/C23H38O5/c1-7-18-12-15(4)19(24)10-9-14(3)11-16(5)21(8-2)28-22(26)13-20(25)17(6)23(18)27/h9-11,15-18,20-21,23,25,27H,7-8,12-13H2,1-6H3/b10-9-,14-11+

Upstream product

• 1403991-98-9 (S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one 
• 635758-46-2 (S)-3-((E)-2-methylpent-2-enoyl)-4-benzyloxazolidin-2-one 
• 40950-55-8 3-((2-acetamidoethyl)thio)-3-oxopropanoic acid 
• 16957-70-3 2-methylpent-2-enoic acid 
• 219610-75-0 (S)-2-((benzyloxy)methyl)butan-1-ol 
• 163457-34-9 (+)-(4S)-3-<(2'R)-2'-((benzyloxy)methyl)butanoyl>-4-benzyl-2-oxazolidinone 
• 102518-92-3 (4S,5R,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethylhept-2-enal 
• 1403991-96-7 (S)-4-benzyl-3-((4S,5R,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethylhept-2-enoyl)oxazolidin-2-one 

Downstream Products

• 58947-83-4 12,13-de-epoxy-12,13-dehydro-20-dihydrorosaramicin 
• 56689-42-0 12,13-de-epoxy-12,13-didehydrorosaramicin 
• 59227-84-8 20-deoxo-20-dihydrorosaramicin 
• 35834-26-5 rosaramicin 
• 80240-61-5 5-O-desosaminyltylonolide 
• 1079242-77-5 5-O-α-L-rhamnosyltylactone 
• 75399-55-2 5-O-α-L-mycarosyltylactone 
• 81661-90-7 5-O-mycaminosyl tylactone 
• 1401-69-0 15-[[(6-deoxy-2,6-di-O-methyl-β-D-allopyranosyl)-oxy]methyl]-6-[[3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-α-L-ribo-hexapyranosyl)-3-(dimethylamino)-β-D-glucopyranosyl]oxy]-16-ethyl-4-hydroxy-5,9,13-trimethyl-2,10-oxo-oxocyclo-hexadeca-11,13-diene-7... 

Relevant articles and documents

Probing Selectivity and Creating Structural Diversity Through Hybrid Polyketide Synthases

Engineering polyketide synthases (PKS) to produce new metabolites requires an understanding of catalytic points of failure during substrate processing. Growing evidence indicates the thioesterase (TE) domain as a significant bottleneck within engineered PKS systems. We created a series of hybrid PKS modules bearing exchanged TE domains from heterologous pathways and challenged them with both native and non-native polyketide substrates. Reactions pairing wildtype PKS modules with non-native substrates primarily resulted in poor conversions to anticipated macrolactones. Likewise, product formation with native substrates and hybrid PKS modules bearing non-cognate TE domains was severely reduced. In contrast, non-native substrates were converted by most hybrid modules containing a substrate compatible TE, directly implicating this domain as the major catalytic gatekeeper and highlighting its value as a target for protein engineering to improve analog production in PKS pathways.

Macrolide biosynthesis. Tylactone formation involves the processive addition of three carbon units

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