High Capacity Poly(ethylene glycol) Based Amino Polymers for Peptide and Organic Synthesis

Abstract

A beaded, chemically stable, high capacity amino resin for solid phase synthesis under polar and non-polar conditions is described. By exhaustive reduction of amide carbonyl groups in PEG cross linked poly(ethylene glycol)-poly(-acrylamide) copolymer (PEGA) a significant increase in functional amino groups is obtained. Furthermore, a resin containing 90% PEG which is free of amide carbonyl groups is produced. The polymer was characterized by IR spectroscopy and the macroscopic properties of the beads were analyzed by microscopy. Excellent swelling properties in various solvents ranging from water to DCM were demonstrated. The chemical stability of the polymer in various reagents and solvents was investigated and changes in resin properties monitored by IR spectroscopy.The mechanical stability of the resin was analyzed by measurement of compressive strain. The unique three dimensional structure of the swelled polyethylene glycol network facilitate fast and unhindered diffusion of reagents and the support is excellent for synthesis of peptides or peptide mimetics, which can be produced in high yield/reaction volume. The efficacy of the new resin in solid phase synthesis was demonstrated by synthesizing an a-MSH peptide fragment. A cyclic peptide mimetic was also synthesized on the new resin by the Cu (1) catalyzed intra molecular cyclo addition of alkyne and azide to form a triazole acting as a disulphide mimetic entity in very high yield and purity.

Porous polymer particles—A comprehensive guide to synthesis, characterization, functionalization and applications

“…Another common way to analyze mechanical strength of particles with sizes down to 2 µm in diameter is via compressing a single particle between two plates and measuring the deformation [294][295][296][297] by several ways such as microscopy [298] or weighing [299]. This technique is more suitable for monodisperse spherical particles since the measurement is generally performed on a single particle.…”

“…Although there are numerous studies on CuAAC functionalization of nonporous polymers [280,298,328,[336][337][338][339][340][341][342][343][344][345][346][347][348][349][350][351], silica [352][353][354] and metal particles [355], the amount of publications on porous polymer particles is limited. Finn et al [356] described the click functionalization of a commercial porous agarose resin for affinity chromatography.…”

Click to Join Peptides/Proteins Together

“…[26] In their studies, the linear peptide 21, in which the azide and alkyne group are introduced onto amino acid side chains, was synthesized by SPPS on a PEGA resin. Then, the intramolecular cyclization, catalyzed by CuI and DIPEA in THF, proceeded smoothly.…”

“…Then, cleavage from the resin produced 76 % of the desired product. [26] A recent study demonstrated double cyclization with the simultaneous formation of two triazoles to mimic the two disulfide bonds in antibacterial bhairpin peptides. [42] The head-to-tail cyclization has frequently been complicated by dimerization and oligomerization.…”

A reação "click" na síntese de 1,2,3-triazóis: aspectos químicos e aplicações

“…Na química de materiais, a reação "click" vem sendo extensivamente utilizada na obtenção de diversos materiais, tais como dendrí-meros, 37,38,[104][105][106][107] polímeros, [108][109][110][111] fases estacionárias modificadas, [119][120][121][122] organogéis, [123][124][125] macrociclos, [134][135][136] dentre outros. Dendrímeros são moléculas formadas a partir de um núcleo polifuncionalizado através do crescimento radial de camadas, de forma repetitiva.…”