24317-94-0Relevant academic research and scientific papers
Substrate Flexibility of the Flavin-Dependent Dihydropyrrole Oxidases PigB and HapB Involved in Antibiotic Prodigiosin Biosynthesis
Couturier, Maxime,Bhalara, Hiral D.,Chawrai, Suresh R.,Monson, Rita,Williamson, Neil R.,Salmond, George P. C.,Leeper, Finian J.
, p. 523 - 530 (2019/11/11)
In the biosynthesis of the tripyrrolic pigment prodigiosin, PigB is a predicted flavin-dependent oxidase responsible for the formation of 2-methyl-3-amylpyrrole (MAP) from a dihydropyrrole. To prove which dihydropyrrole is the true intermediate, both possibilities, 5-methyl-4-pentyl-3,4-dihydro-2H-pyrrole (5 a, resulting from transamination of the aldehyde of 3-acetyloctanal) and 2-methyl-3-pentyl-3,4-dihydro-2H-pyrrole (6, resulting from transamination of the ketone), were synthesised. Only 5 a restored pigment production in a strain of Serratia sp. ATCC 39006 blocked earlier in MAP biosynthesis. PigB is membrane-associated and inactive when its transmembrane domain was deleted, but HapB, its homologue in Hahella chejuensis, lacks the transmembrane domain and is active in solution. Two colourimetric assays for PigB and HapB were developed, and the HapB-catalysed reaction was kinetically characterised. Ten analogues of 5 a were synthesised, varying in the C2 and C3 side chains, and tested as substrates of HapB in vitro and for restoration of pigment production in Serratia ΔpigD in vivo. All lengths of side chain tested at C3 were accepted, but only short side chains at C2 were accepted. The knowledge that 5 a is an intermediate in prodigiosin biosynthesis and the ease of synthesis of analogues of 5 a makes a range of prodigiosin analogues readily available by mutasynthesis.
Microwave assisted synthesis of fragrant jasmone heterocyclic analogues
Pawelczyk, Anna,Zaprutko, Lucjusz
, p. 586 - 591 (2007/10/03)
cis-Jasmone, from jasmonoid group, is an important jasmine odor fragrance compound. The syntheses of new heterocyclic analogues of jasmone were described. Five analogues of this compound were prepared under microwave irradiation and the results of the microwave assisted syntheses were compared with classical, thermally initiated reactions in solvent. Microwave reactions were carried out successfully, and reaction times were significantly reduced to a few minutes. Three of five obtained analogues, pyrrolidinone, oxazolidinone and thiazolidinone demonstrated an interesting, specific odor which was compared with floral, typical jasmine odor of jasmone.
3-Arylcyclohex-2-en-1-ones and 2,6-Diarylcyclohex-2-en-1-ones. New Liquid Crystalline Compounds
Brettle, Roger,Dunmur, David A.,Farrand, Louise D.,Hindley, Nigel J.,Marson, Charles M.
, p. 1663 - 1666 (2007/10/02)
The cyclohex-2-en-1-one unit flanked by one or more aryl rings is shown to provide a new system which can exhibit liquid crystal properties; these new mesogens contain a chiral centre which is both adjacent to a lateral dipolar carbonyl group and its also located in the central core.
Syntheses of Jasmonic Acid Related Compounds and Their Structure-Activity Relationships on the Growth of Rice Seedings
Yamane, Hisakazu,Sugawara, Jun,Suzuki, Yasushi,Shimamura, Etsuko,Takahashi, Nobutaka
, p. 2857 - 2864 (2007/10/02)
Jasmonic acid (JA)-related compounds were synthesized, and their inhibitory activities on rice seedling growth were investigated.Three functions (C-1 CH2COOH or CH2COOCH3, C-2 (Z)-2'-pentenyl or n-pentyl and C-3 ketone or hydroxyl) were essential for exhibiting inhibitory activity in this series of compounds.A dihydro-JA-related compound, 4-acetylnonanoic acid, also showed inhibitory activity similar to JA.
