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Linkers 1,3-dithiane

Routledge A, Abell C, Balasubramanian S. The use of a dithiane-protected benzoin photolabile safety catch linker for solid-phase synthesis. Tetrahedron Lett 1997 38 1227-1230. [Pg.220]

An interesting application of the 3-methoxybenzoin-based photolabile linker has been described in which the dithiane, ( )-(3- 2-(l,3-dithian-2-yl)-l-[(9-fluorenylmethoxy-carbonyl)oxy]-2-phenylethyl)benzyl)oxy] acetic acid (126, Scheme 33), a transiently masked form of the caging moiety, is incorporated into a peptide chain generated by solid-phase synthesis. 248 ... [Pg.136]

A further safety-catch linker is based on a difhiane-protected benzoin (173). It can be activated for cleavage by photolysis according to Scheme 79, after removal of the dithiane protection [194]. It can be applied to the attachment and subsequent release of alcohols and carboxylic acids. A disadvantage is that if activation is performed with a Hg(II) salt, then this must be removed completely in order to avoid problems in assays using proteins as biological targets. [Pg.96]

However, the chromophore in the DMB linker proved to be too sensitive to light, so a dithiane-protected structure, introduced by Chan [35] and Balasubramanian, was used to employ a safety-catch strategy. Using this strategy, peptides could be anchored to the linker by a C-terminal ester bond [36] or by an N-terminal carbamate bond [37] (Scheme 17.10). In a Fmoc-alanine releasing test, the dithiane was deprotected using methyl triflate or periodic acid, and photocleavage resulted in a 92% yield of Fmoc-Ala after 2 h. [Pg.479]

Routl997a Routledge, A., Abell, C. and Balasubramanian, S., The Use of a Dithiane Protected Benzoin Photolabile Safety Catch Linker for Solid-Phase Synthesis, Tetrahedron Lett., 38 (1997) 1227-1230. [Pg.158]

The safety-catch linker 34 developed by Balasubramanian and Lee in 1999 combines preactivation of the linker and cleavage through irradiation (pho-tocleavable safety-catch linker) [66-69]. Preactivation of the linker means removal of the dithiane protection can be performed oxidatively by addition of H5IO6 or by addition of MeOTf (Scheme 5) while subsequent cleavage of the linker occurs with irradiation of 350 nm. The chemical stabiUty of the linker has been tested imder reductive/oxidative, basic/acidic and nucleophilic conditions as well as in ester coupling and carbon-carbon bond-forming reactions. The Balasubramanian linker is only one example of an ester hnker class called photocleavable linkers. Some of them are summarized in Fig. 3 [70-77]. [Pg.9]

Dithianes are known as protecting groups for safety-catch linkers [66] but they can also be used as Unker systems for the synthesis of either carbonyl-containing or aliphatic compounds. Bertini et al. [280] synthesized the first... [Pg.47]

In order to avoide premature photolysis of the benzoin linker by adventitious room light during the course of the synthesis, the dithiane-protected 3-alkoxybenzoin (49a) has been suggested as a UV-inactive linker. The dithiane-protected 3-alkoxybenzoin (49a) released less than 3% of the product after irradiation at 350 nm. The photosensitivity is restored by hydrolysis of the dithiane prior to photocleavage, as illustrated in Eq. (69.22). Photolysis of the deprotected linker resulted in a 75% yield of the product... [Pg.1409]


See other pages where Linkers 1,3-dithiane is mentioned: [Pg.487]    [Pg.682]    [Pg.487]    [Pg.682]    [Pg.48]    [Pg.188]    [Pg.143]    [Pg.53]    [Pg.136]    [Pg.478]    [Pg.450]    [Pg.37]    [Pg.243]    [Pg.37]    [Pg.16]   
See also in sourсe #XX -- [ Pg.487 , Pg.488 ]




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