67919-87-3

Basic information

• Product Name: Isopseudomonic acid A
• CAS NO: 67919-87-3
• Molecular Weight: 500.63
• Mol File: 67919-87-3.mol

Chemical Properties

• CAS DataBase Reference: Isopseudomonic acid A(CAS DataBase Reference)
• NIST Chemistry Reference: Isopseudomonic acid A(67919-87-3)
• EPA Substance Registry System: Isopseudomonic acid A(67919-87-3)

Safety Data

• Hazardous Substances Data: 67919-87-3(Hazardous Substances Data)

Upstream product

• 40980-51-6 pseudomonic acid B 
• 944069-01-6 mupirocin F₁ 
• 32742-34-0 1,5-Anhydro-D-arabinitol 
• 75452-42-5 C₃₂H₄₄O₅Si 
• 87678-99-7 1-{(2S,3R,4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3,4-dihydroxy-tetrahydro-pyran-2-yl}-propan-2-one 
• 87678-98-6 1-{(2S,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5,6-dihydro-2H-pyran-2-yl}-propan-2-one 
• 115888-77-2 (E)-5,9-anhydro-6,7-O-cyclohexylidene-2,3,4,8-tetradeoxy-8-C-(ethoxycarbonyl)methyl-3-methyl-D-allo-non-2-enitol 
• 115888-76-1 (E)-5,9-anhydro-6,7-O-cyclohexylidene-2,3,4,8-tetradeoxy-8-C-(ethoxycarbonyl)methyl-3-methyl-D-allo-non-2-enal 
• 85620-85-5 3R-3,6-dihydro-2H-pyranyl-N,N-dimethylacetamide 
• 87614-56-0 5S-iodo-1S,6S-3,7-dioxabicyclo<4,3,0>nonan-8-one 
• 50-69-1 D-Arabinose 
• 85620-84-4 1,5-anhydro-2,3-dideoxy-D-glycero-pent-2-enitol 
• 87641-25-6 C₃₆H₅₀O₆Si 
• 87614-60-6 2-{(2S,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5,6-dihydro-2H-pyran-2-yl}-N,N-dimethyl-acetamide 

Downstream Products

• 71980-98-8 pseudomonic acid C 

Relevant articles and documents

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.

Purification of Mupirocin

A method for purification of the antibiotic mupirocin (pseudomonic acid A) which comprises: a) Causing or allowing precipitation of mupirocin from an aqueous solution thereof; b) Recovering the precipitate; c) Dissolving the recovered precipitate in an organic solvent.

ENANTIOSPECIFIC TOTAL SYNTHESIS OF PSEUDOMONIC ACIDS FROM ARABINOSE

The enantiospecific synthesis of pseudomonic acids from arabinose is described.