74758-60-4

Usage

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

• 144450-37-3 C₉⁽¹³⁾CH₁₉NO₃S 
• 144450-38-4 ethyl <α-methyl-13C>-(2R,3R)-2-methyl-3-hydroxy-pentanoate 
• 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 
• 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 

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 academic research and scientific papers

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.

Chemoenzymatic Total Synthesis and Structural Diversification of Tylactone-Based Macrolide Antibiotics through Late-Stage Polyketide Assembly, Tailoring, and C-H Functionalization

Polyketide synthases (PKSs) represent a powerful catalytic platform capable of effecting multiple carbon-carbon bond forming reactions and oxidation state adjustments. We explored the functionality of two terminal PKS modules that produce the 16-membered tylosin macrocycle, using them as biocatalysts in the chemoenzymatic synthesis of tylactone and its subsequent elaboration to complete the first total synthesis of the juvenimicin, M-4365, and rosamicin classes of macrolide antibiotics via late-stage diversification. Synthetic chemistry was employed to generate the tylactone hexaketide chain elongation intermediate that was accepted by the juvenimicin (Juv) ketosynthase of the penultimate JuvEIV PKS module. The hexaketide is processed through two complete modules (JuvEIV and JuvEV) in vitro, which catalyze elongation and functionalization of two ketide units followed by cyclization of the resulting octaketide into tylactone. After macrolactonization, a combination of in vivo glycosylation, selective in vitro cytochrome P450-mediated oxidation, and chemical oxidation was used to complete the scalable construction of a series of macrolide natural products in as few as 15 linear steps (21 total) with an overall yield of 4.6%.