High-throughput synthesis: principles and practices by Irving Sucholeiki

By Irving Sucholeiki

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Instead of an ester, acid, or amide appendage, only a methyl group was left on the cleaved scaffold. Later, this concept of a general linker that would leave no trace, or that would be “traceless” on the cleaved scaffold, took hold with the goal being that hydrogen would be the only acceptable group allowed on the cleaved scaffold. One of the first of these types of linkers employed an arylsilane linkage 45 and Copyright © 2001 Marcel Dekker, Inc. 22 Sucholeiki Figure 6 Traceless linkers used in solid phase organic synthesis.

Pillai synthesized a peptide on a support consisting of 1% cross-linked polystyrene containing a 3-nitro-4-N-methylaminomethyl moiety (42). Pillai showed that one can successfully cleave the polymer-bound carbon-nitrogen bond upon irradiation with 350-nm light to give C-terminal N-methylated peptide amides [76]. Only a handful of research groups have exploited the use of photocleavable linkers in the production of combinatorial libraries. One photosensitive linker that has found broad use in both peptide and nonpeptide solid phase synthesis is the 6-nitroveratryl-based linker (43), which was based on an earlier photosensitive protecting group (Fig.

22 Sucholeiki Figure 6 Traceless linkers used in solid phase organic synthesis. used hydrogen fluoride to cleave the scaffold off the support (Fig. 6) [81]. Later this type of linker was modified by other researchers to incorporate a silyl halide handle to make it easier to attach and cleave molecules from the support (46, Fig. 6) [82]. VII. A BRIEF SUMMARY OF ANALYTICAL METHODS AVAILABLE FOR MONITORING THE SOLID SUPPORT No matter what support and linker one uses in a solid phase synthesis approach, some analytical method must be used to evaluate the success or failure of that approach [83].

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