- 著者
- Toshiaki Taira Yuki Ishizaki Shusei Yamamoto Kenichi Sakai Hideki Sakai Tomohiro Imura
- 出版者
- Japan Oil Chemists' Society
- 雑誌
- Journal of Oleo Science (ISSN:13458957)
- 巻号頁・発行日
- vol.68, no.12, pp.1223-1230, 2019 (Released:2019-12-01)
- 参考文献数
- 42
- 被引用文献数
- 1 1
We report the synthesis of amphiphilic dodecenyl phosphonic acid PC12 from vinylphosphonic acid, a reactive phosphonic acid intermediate. The trans-P-C=C moiety enabled PC12 to disperse well in water. Surface tension and dynamic light scattering measurements revealed that PC12 exhibited high surface activity and reduced the surface tension of water from 72.0 to 23.6 mN/m, thereby resulting in the spontaneous formation of aggregates even in a dilute aqueous solution (critical aggregation concentration (CAC) = 4.8 × 10–4 M). In contrast to modern lipids with double-tailed structures, the PC12 of simple singletailed structure spontaneously formed bilayered vesicles, without an external energy supply. Compared with the strength of hydrogen bonds formed by the long, saturated alkyl chain of dodecyl phosphonic acid (DPA), the strength of PC12 intermolecular hydrogen bonds was weaker. The melting point of PC12 was approximately 20°C lower than that of DPA. These results indicate that the trans-P-C=C moiety was considerably important for spontaneous vesicle formation in water. Preliminary modeling of the morphological transitions of the closed bilayer structures in the vesicles was then conducted, by varying the pH and adding an α-helical peptide scaffold.
- 著者
- Masaaki Konishi Tomotake Morita Tokuma Fukuoka Tomohiro Imura Shingo Uemura Hiroyuki Iwabuchi Dai Kitamoto
- 出版者
- Japan Oil Chemists' Society
- 雑誌
- Journal of Oleo Science (ISSN:13458957)
- 巻号頁・発行日
- vol.67, no.4, pp.489-496, 2018 (Released:2018-04-01)
- 参考文献数
- 34
- 被引用文献数
- 18 40
We discovered that Candida floricola ZM1502 is capable of selectively producing the promising hydrophilic biosurfactants, acid-form sophorolipids (SLs), from glycerol. However, productivity was very low (approximately 3.5 g L–1) under the initial culture conditions. Here, we describe the design of culture medium for abundant production of acid-form SLs by C. floricola ZM1502 using waste glycerol and hydrophobic substrates in order to develop a method for SL production and disposal of waste glycerol produced by oleo-chemical industries. Urea provided the best nitrogen source for acid-form SL production from glycerol among four nitrogen sources tested [urea, NaNO3, NH4NO3, and (NH4)2SO4]. Among carbon sources we compared, hydrophobic substrates (soybean oil and oleic acid) led to productivities of approximately 20 g L–1, indicating that hydrophobic substrates provided fatty acid moieties for SL production. Addition of olive oil and oleic acid to waste glycerol enhanced acid-form SL production to 42.1 ± 0.9 and 37.5 ± 3.4 g L–1, respectively. To develop a potential industrial process, we explored other suitable hydrophobic substrates for SL production, which were obtained on site from oleo-chemical industries. Alkyl C18 esters (Pastell M-182), along with waste glycerol, increased acid-form SL production to 48.0 ± 3.4 g L–1 over a 7-d period. Furthermore, we demonstrated abundant production of acidic SLs at the mini-jar fermenter scale, obtaining 169 g L–1 over 180 h using a fed-batch cultivation technique. Efficient acid-form SL production by C. floricola could have a great impact on the development of bio-industrial processes using waste glycerol as a substrate.