140715-85-1

Basic information

• Product Name: fumiquinazoline A
• Synonyms: fumiquinazoline A
• CAS NO: 140715-85-1
• Molecular Formula: C24H23N5O4
• Mol File: 140715-85-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: fumiquinazoline A(CAS DataBase Reference)
• NIST Chemistry Reference: fumiquinazoline A(140715-85-1)
• EPA Substance Registry System: fumiquinazoline A(140715-85-1)

Safety Data

• Hazardous Substances Data: 140715-85-1(Hazardous Substances Data)

Upstream product

• 169626-35-1 (1S,4R)-4-[(1H-indol-3-yl)methyl]-1-methyl-1,2-dihydro-4H-pyrazino[2,1-b]quinazoline-3,6-dione 
• 56-41-7 L-alanin 
• 118-92-3 anthranilic acid 
• 496961-79-6 C₂₆H₂₄Cl₃N₃O₈ 
• 496961-80-9 C₂₆H₂₄Cl₃N₃O₈ 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 316828-53-2 N-19-benzyloxycarbonyl-fumiquinazoline A 
• 140715-86-2 (-)-fumiquinazoline C 
• 422319-37-7 methyl (2S,9S,9aR,αR)-9-hydroxy-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-2,3,9,9a-tetrahydro-1H-imidazo(1,2-a)indole-9-propanoate 
• 316828-49-6 C₄₇H₄₁N₅O₉ 
• 316828-51-0 C₄₇H₃₉N₅O₈ 
• 316828-44-1 methyl (αR,2S,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate 
• 316828-35-0 N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester 
• 316828-48-5 C₂₉H₂₆N₄O₆ 

Relevant articles and documents

Fumiquinazolines, novel metabolites of a fungus isolated from a saltfish

Fumiquinazolines A, B and C, exhibiting moderate cytotoxicity, were isolated from the mycelium of a strain of Aspergillus fumigatus which existed in the gastrointestinal tract of the saltwater fish Pseudolabrus japonicus. Their structures were elucidated by spectroscopic and X-ray diffraction analyses and chemical evidence.

Complexity generation in fungal peptidyl alkaloid biosynthesis: Oxidation of fumiquinazoline A to the heptacyclic hemiaminal fumiquinazoline C by the flavoenzyme Af12070 from aspergillus fumigatus

The human pathogen Aspergillus fumigatus makes a series of fumiquinazoline (FQ) peptidyl alkaloids of increasing scaffold complexity using l-Trp, 2 equiv of l-Ala, and the non-proteinogenic amino acid anthranilate as building blocks. The FQ gene cluster encodes two non-ribosomal peptide synthetases (NRPS) and two flavoproteins. The trimodular NRPS Af12080 assembles FQF (the first level of complexity) while the next two enzymes, Af12060 and Af12050, act in tandem in an oxidative annulation sequence to couple alanine to the indole side chain of FQF to yield the imidazolindolone-containing FQA. In this study we show that the fourth enzyme, the monocovalent flavoprotein Af12070, introduces a third layer of scaffold complexity by converting FQA to the spirohemiaminal FQC, presumably by catalyzing the formation of a transient imine within the pyrazinone ring (and therefore acting in an unprecedented manner as an FAD-dependent amide oxidase). FQC subsequently converts nonenzymatically to the known cyclic aminal FQD. We also investigated the effect of substrate structure on Af12070 activity and subsequent cyclization with a variety of FQA analogues, including an FQA diastereomer (2′-epi-FQA), which is an intermediate in the fungal biosynthesis of the tremorgenic tryptoquialanine. 2′-epi-FQA is processed by Af12070 to epi-FQD, not epi-FQC, illustrating that the delicate balance in product cyclization regiochemistry can be perturbed by a remote stereochemical center.

Total syntheses of (-)-fumiquinazolines A, B, and I.

[structure] The first total syntheses of (-)-fumiquinazolines A, B, and I have been accomplished efficiently using the Pd-catalyzed cyclization of an iodoindole carbamate to construct the imidazoindolone moiety and the dehydrative cyclization of a diamide