Palladium-catalysed reactions in solid phase organic synthesis

Bräse, Stefan; Kirchhoff, Jan H.; Köbberling, J.

doi:10.1016/s0040-4020(02)01425-4

Cited by 160 publications

(53 citation statements)

References 247 publications

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“…[101] Post-polymerization modification using one of these reactions requires polymers with alkyl or aryl halide, alkene, alkyne, boronic acid or ester, or organotin functional handles. p-Bromostyrene can be polymerized by controlled radical and anionic polymerization ( Table 1).…”

Section: Modification Of Polymers By Pd-catalyzedmentioning

confidence: 99%

Synthesis of Functional Polymers by Post‐Polymerization Modification

2008

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Post-polymerization modification is based on the direct polymerization or copolymerization of monomers bearing chemoselective handles that are inert towards the polymerization conditions but can be quantitatively converted in a subsequent step into a broad range of other functional groups. The success of this method is based on the excellent conversions achievable under mild conditions, the excellent functional-group tolerance, and the orthogonality of the post-polymerization modification reactions. This Review surveys different classes of reactive polymer precursors bearing chemoselective handles and discusses issues related to the preparation of these reactive polymers by direct polymerization of appropriately functionalized monomers as well as the post-polymerization modification of these precursors into functional polymers.

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Section: Modification Of Polymers By Pd-catalyzedmentioning

confidence: 99%

Synthesis of Functional Polymers by Post‐Polymerization Modification

2008

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“…Allylic groups have been used as the common orthogonal protecting groups for on-resin cyclization with Fmoc strategy [12,13]. For example, allyl (All) and allyloxycarbonyl (Aloc) groups, for protecting carboxylic and amino groups, respectively, enable the construction of a lactam bridge selectively between carboxylic and amino groups while the peptide is still attached to the resin.…”

Section: Introductionmentioning

confidence: 99%

Solid‐phase synthesis of tailed cyclic RGD peptides using glutamic acid: unexpected glutarimide formation

Zhu

Marchant

2007

Journal of Peptide Science

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To provide multiple conjugating sites on cyclic peptides for their increasing biomedical applications, a tailed cyclic RGD peptide, c[RGDfE(GGGKK-NH 2 )] was designed with c(RGDfE) linked through Glu to a tail consisting of a spacer of three Gly residues and a linker of two Lys residues. The spacer is used to increase the mobility and binding ability of the c(RGDfE) ligand, and the linker is used to proved multiple active sites for conjugating other molecules or biomaterials. We found that the sequence of Glu(Gly)-OAll leads to glutarimide formation, which disrupts the formation of cyclic RGD peptides. However, our results show that glutarimide formation is sequence dependent and can be inhibited by incorporating an amino acid like Lys(Boc) with steric hindrance from the protecting group. To prevent glutarimide formation, Ser(tBu) was used to replace the glycine in the GGG spacer adjacent to the residue of Glu, and a tailed cyclic RGD peptide, c[RGDfE(SGGKK-NH 2 )] was successfully obtained.

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“…[4,5] Reflecting this driving force, a wide range of standard solution-phase reactions have now been adapted for solid-supported synthesis, and these have been the subject of some excellent reviews. [2,[6][7][8] To accommodate the growing number of reactions carried out on solid-supported substrates, large numbers of sophisticated linker units have been developed and are now routinely employed in solid-phase synthesis. Typically, linker units are conveniently grouped according to the functionality left at the "cleavage site" in the target molecule (Scheme 1), and can be classified as traditional/classical (the site of attachment to the resin remains following cleavage), traceless (hydrogen residue left after cleavage) or diversity linkers.…”

Section: General Introductionmentioning

confidence: 99%

Diversity Linker Units for Solid‐Phase Organic Synthesis

Scott

Steel

2006

Eur J Org Chem

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In recent years an ever‐increasing number of traditional solution‐phase reactions have been adapted for solid‐phase organic synthesis (SPOS) because of the ease of application of solid‐phase techniques to combinatorial chemistry and high‐throughput screening. To accommodate the growing number of reactions being attempted on solid supports, new linker units continue to be reported in the literature. Linker units are typically grouped according to the functionality left at the “cleavage site” in the target molecule, and are normally classified as traditional (polar functionality remains following cleavage) or traceless (hydrogen residue left after cleavage) linkers. As the field continues to expand, however, more advanced linker units have been reported, which utilise the cleavage step in SPOS to incorporate additional diversity into target libraries. These linker units have been termed “diversity” or “multifunctional” linker units, and in this microreview we introduce this aspect of the field, giving representative examples indicating key stages of development including the linker units recently designed in our laboratory. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Palladium-catalysed reactions in solid phase organic synthesis

Cited by 160 publications

References 247 publications

Synthesis of Functional Polymers by Post‐Polymerization Modification

Synthesis of Functional Polymers by Post‐Polymerization Modification

Solid‐phase synthesis of tailed cyclic RGD peptides using glutamic acid: unexpected glutarimide formation

Diversity Linker Units for Solid‐Phase Organic Synthesis

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