Caged compounds with a steroid skeleton: synthesis, liposome-formation and photolysis

Watanabe, Soichiro; Hiratsuka, Remi; Kasai, Yosuke; Munakata, Kazunori; Takahashi, Yasuhiro; Iwamura, Michiko

doi:10.1016/s0040-4020(02)00077-7

Cited by 8 publications

(4 citation statements)

References 16 publications

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“…General procedure A and chromatography (pentane) produced the title compound as a colorless oil (0.31 g, 64%), whose spectroscopic properties matched those previously reported …”

Section: Methodssupporting

confidence: 78%

“…Suffix “a” refers to substrates, and suffix “b” refers to products. MNP and compounds 3a , 7a , 10a , and 20a were prepared according to literature methods.…”

Section: Methodsmentioning

confidence: 99%

“…General procedure A and chromatography (pentane) produced the title compound as a colorless oil (0.31 g, 64%), whose spectroscopic properties matched those previously reported. 22 (R)-Triethyl(5-methyl-2-(prop-1-en-2-yl)hexyloxy)silane (6b). General procedure A and chromatography (hexanes) produced a colorless oil (0.69 g, 70%).…”

Section: -(Butamentioning

confidence: 99%

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Regioselective Semihydrogenation of Dienes

et al. 2011

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A one-pot, three-step strategy for the regioselective semihydrogenation of dienes is described. This procedure uses 9-BBN-H as a temporary protective group for alkenes. Yields range from 55% to 95%, and the reaction is tolerant of a variety of common functional groups. Additionally, the final elimination step of the sequence can be replaced with a peroxide-mediated alkylborane oxidation, generating regioselectively semihydrogenated product alcohols.

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“…General procedure A and chromatography (pentane) produced the title compound as a colorless oil (0.31 g, 64%), whose spectroscopic properties matched those previously reported …”

Section: Methodssupporting

confidence: 78%

“…Suffix “a” refers to substrates, and suffix “b” refers to products. MNP and compounds 3a , 7a , 10a , and 20a were prepared according to literature methods.…”

Section: Methodsmentioning

confidence: 99%

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Regioselective Semihydrogenation of Dienes

et al. 2011

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“…38 Biomolecules with an amino group formed caged compounds upon reaction with an o-nitrobenzyl p-nitrophenyl carbonate, while a carboxylic acid moiety was caged with an o-nitrobenzyl diazo compound. 39 Irradiation of the caged compounds released the amino and carboxylic acid groups. Time-resolved FTIR was used to directly measure photorelease from γ-(α-carboxy-2-nitrobenzyl)glutamate on the microsecond time scale.…”

Section: Photocleavable Protecting Groups and Caged Compoundsmentioning

confidence: 99%

11 Organic photochemistry

Boyd¹,

Zopp²

2003

Annu. Rep. Prog. Chem., Sect. B

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This review covers the literature during publication year 2002 concerning organic photochemistry. The general areas of photochemical applications in organic synthesis and mechanistic studies are both covered. This review is selective rather than comprehensive, due to the large volume of publications in this field. Biological photochemistry is not covered.Of particular note in 2002 is the development of a smart photochromic system which links bis-naphthopyrans through a bis-thiophene moiety. 1 The thiophene tether undergoes a time-dependent change during irradiation, with its electron-donating ability varying due to hybridization changes at the spirocyclic carbon. The development of orthogonal photocleavable protecting groups, with intramolecular or intermolecular discrimination, was described. 2 Chiral discrimination in excited-state proton transfer was demonstrated through an enhanced proton transfer rate from 5,8-dicyano-2-naphthol to enantiopure 2-butanol, compared to the racemic solvent. 3 Progress in photoinduced asymmetric induction for photocyclization and geometric isomerizations was reported. [4][5][6] The highest levels of asymmetric induction were achieved in zeolites in combination with ionic or neutral chiral auxiliaries.

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Biologisch aktive Moleküle mit “Lichtschalter”

2006

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Biologisch aktive Verbindungen, die auf Licht reagieren, bieten experimentelle Möglichkeiten, die sonst nur sehr schwierig zu realisieren sind. Da Licht z. B. mit Lasern und (konfokalen) Mikroskopen punktgenau eingesetzt werden kann, sind schnelle Konzentrationssprünge der aktiven Form von Molekülen mit exakter räumlicher, zeitlicher und dosierungsbezogener Steuerung möglich. Die Entwicklung derartiger Strategien reicht bis in die 70er Jahre zurück. Dieser Aufsatz fasst neue Entwicklungen der letzten fünf Jahre zusammen und behandelt “kleine Moleküle”, Proteine und Nucleinsäuren, die entweder durch Licht irreversibel aktiviert werden (“photoaktivierbare Verbindungen”) oder reversibel zwischen einem aktiven und einem inaktiven Zustand geschaltet werden.

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Caged compounds with a steroid skeleton: synthesis, liposome-formation and photolysis

Cited by 8 publications

References 16 publications

Regioselective Semihydrogenation of Dienes

Regioselective Semihydrogenation of Dienes

11 Organic photochemistry

Biologisch aktive Moleküle mit “Lichtschalter”

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