71980-98-8

Usage

Uses

Used in Pharmaceutical Industry:
9-[[(2E)-4-[[(2S,3R,4R,5S)-3α,4α-Dihydroxy-5β-[(2E,4S,5S)-5-hydroxy-4-methyl-2-hexenyl]tetrahydro-2H-pyran]-2β-yl]-3-methyl-2-butenoyl]oxy]nonanoic acid is used as an antibiotic agent for treating bacterial infections. It is an analogue of Pseudomonic Acid D, which is isolated from Pseudomonas fluorescens, a bacterium known for its antimicrobial properties.
Used in Cosmetic Industry:
9-[[(2E)-4-[[(2S,3R,4R,5S)-3α,4α-Dihydroxy-5β-[(2E,4S,5S)-5-hydroxy-4-methyl-2-hexenyl]tetrahydro-2H-pyran]-2β-yl]-3-methyl-2-butenoyl]oxy]nonanoic acid can be used as an active ingredient in cosmetic products due to its potential antimicrobial and anti-inflammatory properties. It may help in the development of skincare products that promote skin health and prevent infections.
Used in Research and Development:
9-[[(2E)-4-[[(2S,3R,4R,5S)-3α,4α-Dihydroxy-5β-[(2E,4S,5S)-5-hydroxy-4-methyl-2-hexenyl]tetrahydro-2H-pyran]-2β-yl]-3-methyl-2-butenoyl]oxy]nonanoic acid is also used in research and development for studying its chemical properties, potential applications, and mechanisms of action. It can contribute to the advancement of knowledge in the fields of chemistry, biology, and medicine.

InChI:InChI=1/C26H44O8/c1-18(16-24(30)33-14-9-7-5-4-6-8-13-23(28)29)15-22-26(32)25(31)21(17-34-22)12-10-11-19(2)20(3)27/h10-11,16,19-22,25-27,31-32H,4-9,12-15,17H2,1-3H3,(H,28,29)/b11-10+,18-16+/t19-,20+,21+,22+,25-,26+/m1/s1

Upstream product

• 73590-30-4 Ethyl monate C 
• 72042-22-9 <2S-<2α(E),3β,4β,5α(2E,4S^*,5R^*)>>-9-<<3-methyl-1-oxo-4--2-butenyl>oxy>nonanoic acid methyl ester 
• 104322-84-1 9-{(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enoyloxy}-nonanoic acid methyl ester 
• 34957-73-8 methyl 9-hydroxynonanoate 
• 104322-71-6 (2S,3R,4R)-4-Benzyloxy-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(3-methyl-but-2-enyl)-butane-1,3-diol 
• 89726-74-9 <3aS-<3aα,4α,7aα,7α(2E,4S^*,5R^*)>>-3-oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolopyran-4-yl>-2-propanone 
• 107148-24-3 <3aR-(3aα,4α,7α,7aα)>-tetrahydro-N,N,2,2-tetramethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetamide 
• 107148-28-7 <3aS-<3aα,4α,7aα,7α(2E,4S^*,5R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-7-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolo<4,5-c>pyran 
• 89726-76-1 9-((E)-4-{(3aS,4S,7S,7aR)-7-[(E)-(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl}-3-methyl-but-2-enoyloxy)-nonanoic acid methyl ester 
• 107148-27-6 <3aS-<3aα,4α,7aα,7α(3E,2R^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester 
• 78088-28-5 ethyl (2S,3S)-3-hydroxy-2-methylbutanoate 
• 115118-79-1 *,R^*)>-5,6-dihydro-N-(1-phenylethyl)-2H-pyran-2-acetamide 
• 89726-72-7 Methanesulfonic acid (2S,3S)-1-[1-benzenesulfonyl-2-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyl ester 
• 85576-60-9 (2S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl butanal 

Relevant academic research and scientific papers

Selected Mutations Reveal New Intermediates in the Biosynthesis of Mupirocin and the Thiomarinol Antibiotics

Thiomarinol and mupirocin are assembled on similar polyketide/fatty acid backbones and exhibit potent antibiotic activity against methicillin-resistant Staphylococcus aureus (MRSA). They both contain a tetrasubstituted tetrahydropyran (THP) ring that is essential for biological activity. Mupirocin is a mixture of pseudomonic acids (PAs). Isolation of the novel compound mupirocin P, which contains a 7-hydroxy-6-keto-substituted THP, from a ΔmupP strain and chemical complementation experiments confirm that the first step in the conversion of PA-B into the major product PA-A is oxidation at the C6 position. In addition, nine novel thiomarinol (TM) derivatives with different oxidation patterns decorating the central THP core were isolated after gene deletion (tmlF). These metabolites are in accord with the THP ring formation and elaboration in thiomarinol following a similar order to that found in mupirocin biosynthesis, despite the lack of some of the equivalent genes. Novel mupirocin–thiomarinol hybrids were also synthesized by mutasynthesis.

Enzymatic basis of "hybridity" in thiomarinol biosynthesis

Thiomarinol is a naturally occurring double-headed antibiotic that is highly potent against methicillin-resistant Staphylococcus aureus. Its structure comprises two antimicrobial subcomponents, pseudomonic acid analogue and holothin, linked by an amide bond. TmlU was thought to be the sole enzyme responsible for this amide-bond formation. In contrast to this idea, we show that TmlU acts as a CoA ligase that activates pseudomonic acid as a thioester that is processed by the acetyltransferase HolE to catalyze the amidation. TmlU prefers complex acyl acids as substrates, whereas HolE is relatively promiscuous, accepting a range of acyl-CoA and amine substrates. Our results provide detailed biochemical information on thiomarinol biosynthesis, and evolutionary insight regarding how the pseudomonic acid and holothin pathways converge to generate this potent hybrid antibiotic. This work also demonstrates the potential of TmlU/HolE enzymes as engineering tools to generate new "hybrid" molecules. The biosynthetic mechanism responsible for generating the antibiotic thiomarinol was elucidated. In contrast to previous hypotheses, TmlU acts as a CoA-ligase and works in tandem with a second enzyme, acyltransferase HolE, to link two antimicrobial warheads pseudomonic acid and holothin, creating a hybrid antibiotic (see scheme).

Total Synthesis of Pseudomonic Acid C

Two approaches to the synthesis of aldehyde 28, a key intermediate in the total synthesis of pseudomonic acid C, were developed.One asymmetric route from the chiral hydroxy ester 11 proceeded in 13 steps via the hydroxy lactone 17.A shorter approach involved the Lewis acid catalyzed cycloaddition of formaldehyde to the chiral diene 23a to give 22a, which was separated from its diastereomer and then converted into 28 in seven steps.The introduction of the C-8 side chain was initially accomplished by Julia coupling of 28 with the sulfone anion derived from 40 to give the olefin 34.The stereoselective preparation of 34 was also carried out, via the ester 46a, by a novel ester enolate Claisen rearrangement of the silyl-protected glycolate ester 44.A third approach directed toward the synthesis of the side chain entailed controlling the C-10 stereochemistry of the benzyl-protected glycolate ester 48 by reduction of a precursor propargyl ketone 27 with Alpine borane.Ester enolate Claisen rearrangement then gave the ester 46b with excellent stereocontrol.

Total Synthesis of Pseudomonic Acid C

A convergent total synthesis of pseudomonic acid C from L-lyxose is described in which a highly stereoselective free-radical C-C bond construction plays a key role.

ENANTIOSPECIFIC TOTAL SYNTHESIS OF PSEUDOMONIC ACIDS FROM ARABINOSE

The enantiospecific synthesis of pseudomonic acids from arabinose is described.

The Chemistry of Pseudomonic Acid. Part 5. Structure and Chemistry of Pseudomonic Acid C. X-Ray Crystal Structure of Ethyl Monate C

A third and minor antibiotic component, designated pseudomonic acid C (1a), has been isolated from cultures of the strain Pseudomonas fluorescens NCIB 10586 which produced the structurally related pseudomonic acid A (2a) and B (3).The structure and stereochemistry of the acid (1a) have been confirmed by single-crystal X-ray analysis of the derived ethyl monate C (1f).Pseudomonic acid A has been converted stereospecifically into pseudomonic acid C in high yield.The epoxidation and the acid- and base-stability of pseudomonic acid C have been studied.