- MODIFIED AMINE LIPIDS
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The disclosure provides ionizable amine lipids and salts thereof (e.g., pharmaceutically acceptable salts thereof) useful for the delivery of biologically active agents, for example delivering biologically active agents to cells to prepare engineered cells. The ionizable amine lipids disclosed herein are useful as ionizable lipids in the formulation of lipid nanoparticle-based compositions.
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Page/Page column 240-241
(2020/07/04)
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- Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca
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The volatiles released by Micromonospora aurantiaca were collected by means of a closed-loop stripping apparatus (CLSA) and analysed by GC-MS. The headspace extracts contained more than 90 compounds from different classes. Fatty acid methyl esters (FAMEs) comprised the major compound class including saturated unbranched, monomethyl and dimethyl branched FAMEs in diverse structural variants: Unbranched, α-branched, γ-branched, (ω-1)-branched, (ω-2)-branched, α-and (ω-1)-branched, γ-and (ω-1)-branched, γ-and (ω-2)-branched, and γ-and (ω-3)-branched FAMEs. FAMEs of the last three types have not been described from natural sources before. The structures for all FAMEs have been suggested based on their mass spectra and on a retention index increment system and verified by the synthesis of key reference compounds. In addition, the structures of two FAMEs, methyl 4,8-dimethyldodecanoate and the ethyl-branched compound methyl 8-ethyl-4-methyldodecanoate were deduced from their mass spectra. Feeding experiments with isotopically labelled [ 2H10]leucine, [2H10]isoleucine, [2H8]valine, [2H5]sodium propionate, and [methyl-2H3]methionine demonstrated that the responsible fatty acid synthase (FAS) can use different branched and unbranched starter units and is able to incorporate methylmalonyl-CoA elongation units for internal methyl branches in various chain positions, while the methyl ester function is derived from S-adenosyl methionine (SAM).
- Dickschat, Jeroen S.,Bruns, Hilke,Riclea, Ramona
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supporting information; experimental part
p. 1697 - 1712
(2012/02/04)
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- Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica
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Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.
- Tai, Akira,Syouno, Emi,Tanaka, Kazuki,Fujita, Morifumi,Sugimura, Takashi,Higashiura, Yasutomo,Kakizaki, Masashi,Hara, Hideho,Naito, Tikahiko
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p. 111 - 121
(2007/10/03)
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- The reaction of active zinc with organic bromides
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The oxidative addition of highly reactive zinc to organic bromides shows a pronounced structure-reactivity dependence, in contrast to that shown by other metals. The kinetic and LFER studies suggest a mechanism in which electron transfer (ET) is the rate-determining step of the reaction. Experiments carried out with radical clocks as well as the stereochemical outcome of the reaction support the presence of radicals. The reactivity profiles suggest that the ET has an important component of inner-sphere process in the reaction with alkyl bromides. In the case of aryl halides, Hammet plots are consistent with the participation of aryl halide radical anions as intermediates. The reaction contemplated here can be ascribed as another example of radical-mediated selective reaction, and it has straightforward synthetic applications. Some synthetic work was done in this direction, to demonstrate how this structure-reactivity dependence can be used to obtain selective organozinc formation in unsymmetrical dibromides.
- Guijarro, Albert,Rosenberg, David M.,Rieke, Reuben D.
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p. 4155 - 4167
(2007/10/03)
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- Structure-reactivity relationship in the reaction of highly reactive zinc with alkyl bromides
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Zinc is different! Unlike with magnesium or lithium, the reactions of organic bromides with highly reactive zinc (Zn*) show sensitivity for the structure of the organic moiety. Selective insertions of Zn into tertiary C-Br bonds can be achieved [Eq. (a)]. Competitive kinetic techniques were used to quantify these findings.
- Guijarro, Albert,Rieke, Reuben D.
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p. 1679 - 1681
(2007/10/03)
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