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Solid Phase Synthesis Resins
Varian, Inc. manufactures microporous StratoSpheres resins as supports for solid phase synthesis for use in both medicinal and combinatorial chemistry applications as well as traditional phase peptide synthesis. In both cases, the desired product remains bound to the polymer beads and so isolation simply requires filtration. A further benefit is that an excess of resin can be used to force reactions to completion.
Varian has developed a range of products optimized for each of these different types of application covering batch and parallel synthesis techniques as well as Split and Mix:
- large scale, highly reproducible resins for bulk sythesis applications
- very high purity resins, with minimal risk of leachable contamination
- narrow particle size distributions for maximal homogeneity and rapid filtration
- wide range of resin functionalities and linkage agents
- high loading resins for large quantities of compounds per bead
> PL-AMS Resins
PL-AMS is manufactured from Varian Polymer Lab's PL-CMS resin which enables us to utilize the same degree of control over loading levels for the hugely popular chloromethyl polystyrene resin, with the assured quality this offers.
Application Notes (PDF Format)
> PL-BIG-W Resin
The benzophenone imine of Gly Wang resin, PL-BIG-W, has been developed by Professors William Scott and Martin O'Donnell from Indiana University Purdue University Indianapolis (IUPUI) for the solid phase synthesis of resin-bound unnatural amino acids, peptides and peptidomimetics.
Application Notes (PDF Format)
> PL-BnSH Resin
PL-BnSH Resin is a nucleophilic polymer, which can be used for BnSH Res Michael addition. Kobayashi has exploited this feature to immobilize a number of silyl enol ethers for use in Aldol reactions and Mannich 3 component reactions. The resultant esters have been cleaved by saponification or reduction to yield acids or aldehydes.
Barco has used a polymer supported mercaptomethyl resin to immobilize butanone. This is then converted to a sulfone and used to produce polymer-bound unsaturated ketones for preparing substituted heterocyclic compounds. Other possible applications include scavenging and metal immobilization.
Application Notes (PDF Format)
> PL-Bromoacetal Resin
Bromoacetal resin is a versatile support allowing the production of bicyclic compounds through a cleavage-cyclisation reaction, which results in an essentially 'traceless' reaction.
A range of bicyclic beta turn peptidomimetics prepared via the 1-acyl-3-oxopiperazines motif has been published. In addition the solid phase synthesis of praziquantel, an antiparastic drug used for the treatment of schistomosiasis (Bilharzia or snail fever), has also been reported.
Initially a primary amine is attached to the resin and subsequently acylated.
Following completion of the synthetic cycle, formic acid is commonly used to effect cleavage and cyclisation.
Application Notes (PDF Format)
> PL-Cl-Trt-Cl Resin
PL Cl-Trt-Cl Resin is particularly suited to the generation of protected peptide fragments due to the extremely mild cleavage conditions required. Such resins can also be used for synthesis of alcohols, phenols and amines.
Application Notes (PDF Format)
> PL-CMS Resin
PL-CMS Resin is a contemporary polystyrene-based resin manufactured by a proprietary copolymerization technique. This eliminates the need for Friedel-Crafts functionalization and provides a homogeneous polymer of extremely high purity and optimum reproducibility.
Merrifield Peptide Synthesis
PL-CMS Resin is available in a variety of loadings ranging from 0.4 mmol/g to 1.4 mmol/g (in 0.2 mmol/g increments) with 75-150 µm (100-200 mesh) particle size for Merrifield peptide synthesis techniques. Particle size distribution is narrower than other comparable commercially available resins, and the beads possess a high degree of uniformity. The range of loadings allows for synthesis optimization - larger peptides are generally prepared on lower loading resin; smaller peptides are made more efficiently on higher loading resins.
Combinatorial Synthesis
Varian Polymer Labs has developed the StratoSpheres range of products to meet the demands of combinatorial synthesis, achieving significant increases in loading per bead for optimum performance from small molecule libraries. Using our PL-CMS resin, screening and sequencing can now be reliably achieved from a single bead. High load PL-CMS resins are available in 2.0 mmol/g and 4.0 mmol/g loading in narrow particle size distributions up to 500 µm.
Application Notes (PDF Format)
> PL-DHP Resin
PL-DHP Resin is designed for immobilization of primary and secondary alcohols or phenols. The resulting tetrahydropyranyl ether linkage is stable to most basic reagents but may be cleaved by 95% TFA solution. Alcohols may be immobilized by reaction in the presence of pyridinium p-toluenesulfonate (PPTS). The same reagent can also be used to effect cleavage in an n-butanol/1,2-dichloroethane solvent mixture.
Application Notes (PDF Format)
> PL-FDMPB Resin
PL-FDMPB Resin may be used for the generation of carboxamides or sulfonamides. The resin is prepared from our PL-AMS resin. Anchored through an amide bond, this version is more resistant to acid, allowing higher TFA concentrations to be used during cleavage.
Application Notes (PDF Format)
> PL-FMP Resin, PL-FMPB Resin
PL-FMP Resin is an aldehyde-based resin suitable for attachment of amines via reductive amination. Such materials can then be used to generate carboxamides or sulfonamides, which are cleaved from the resin by treatment with trifluoroacetic acid (TFA).
The resin is derived from the appropriate copolymerized PL-CMS Resin precursor to ensure the highest levels of quality and reproducibility.
PL-FMPB Resins
PL-FMPB Resin is formed by attachment of the 4-(4-formyl-3-methoxyphenoxy-butyric acid linker to our own PL-AMS (Aminomethylstyrene) Resin. The functionality is the same as PL-FMP Resin but with an amide bond there is no risk that cleavage conditions will result in slight loss of the linker from the resin. As with all other formyl resins, this product is designed for generation of carboxamides or sulfonamides. Amines are attached via reductive amination. Following further modification the resulting carboxamide or sulfonamide is released into solution by treatment with TFA.
Application Notes (PDF Format)
> PL-HMBA Resin
PL-HMBA Resin is used for attachment of carboxylic acids, including amino acids. The stability of the ester bond allows acidolysis to be used to cleave side chain protecting groups while the product is still bound to the resin. The ester bond is labile to nucleophiles and so ammonolysis or saponification can be used to generate amides or acids respectively.
Application Notes (PDF Format)
> PL-HMS Resin
PL-HMS (Hydroxymethylstyrene) resin is an alternative to chloromethylstyrene (Merrifield) resin. Carboxylic acids may be esterified to the resin, however, subsequent cleavage of the resultant benzyl ester requires treatment with strong acid such as HF or TFMSA.
The resin is derived from the PL-CMS copolymer resin to ensure the highest levels of quality and reproducibility.
Application Notes (PDF Format)
> PL-HTP Resin
PL-HTP Resin is useful for the preparation of carboxamides and lactams. Acids can be loaded onto the resin and subsequently cleaved by prolonged treatment with suitable primary or secondary amines.
Application Notes (PDF Format)
> PL-ICHO Resin, PL-IND Resin
PL-ICHO Resin may be used to generate secondary amides, sulfonamides and ureas in much the same way as the formylmethoxyphenoxy-based resins PL-FDMP and PL-FMP. Loading of amines is accomplished via reductive amination. Formylindole AMS resins are reportedly easier to cleave, requiring lower concentrations of TFA or shorter exposure times.
PL-IND Resins
PL-IND Resin may be used to generate secondary amides, sulfonamides, ureas and carbamates. The absence of an amide bond linking the functional group to the polymer support means that FTIR can be used to monitor the attachment of amine building blocks. Loading of amines is accomplished via reductive amination. Cleavage of all classes of products is extremely facile, requiring low concentrations of TFA and short exposure times.
Application Notes (PDF Format)
Application Notes (PDF Format)
> PL-IPG Resin, PL-IPG-Diol Resin
PL-IPG Resins
PL-IPG Resin is a vicinal diol resin protected as the acetal form.
The resin was originally developed to enable modification of a single aldehyde group of a symmetrical dialdehyde by acting as a protecting group.
Aldehydes and ketones are attached under anhydrous conditions and may be subsequently cleaved by acidolysis. Loading via an acetal exchange reaction using trimethylorthoformate (TMOF) has also been reported.
In addition, vicinal diol resins have been used to immobilize boronic acids.
PL-IPG-Diol Resins
PL-IPG-Diol Resin is a vicinal diol resin in the unprotected form.
The resin was originally developed to enable modification of a single aldehyde group of a symmetrical dialdehyde by acting as a protecting group.
Aldehydes and ketones are attached under anhydrous conditions and may be subsequently cleaved by acidolysis. Loading via an acetal exchange reaction using trimethylorthoformate (TMOF) has also been reported.
In addition, vicinal diol resins have been used to immobilize boronic acids.
Application Notes (PDF Format)
Application Notes (PDF Format)
> PL-MAMP-OH Resin
PL-MAMP-OH Resin is the stable precursor to MAMP-Cl resin. This versatile resin is designed to enable a variety of amines, including anilines, to be attached to the resin, acylated and then cleaved under mild acidolysis conditions (<25% TFA).
Application Notes (PDF Format)
> PL-MBHA Resin
PL-MBHA Resin is for the synthesis of amides.
Traditional support for solid phase synthesis of peptide amides using Boc chemistry.
Initial amino acids can be coupled directly to the resin using standard coupling techniques.
Cleavage typically requires treatment with very strong acid such as HF or TFMSA. Note: Specialist equipment is required to safely perform HF cleavage operations.
Sometimes Fmoc peptide synthesis is performed on PL-MBHA Resin to allow for removal of side chain protecting groups while the peptide chain remains attached to the resin. HF cleavage then ensures that only the desired unprotected peptide amide is released into solution, free from contamination with cleaved side chain protecting groups.
PL-MBHA Resin can also be used for attachment of linkers in a similar manner to PL-AMS Resin.
Application Notes (PDF Format)
> PL-Oxime Resin
PL-Oxime Resin is designed for the attachment of acids via anhydride activation methods. Displacement by hydrazinolysis, ammonolysis or hydrolysis results in a variety of functional group conversions. Oxime resins have also been used in the synthesis of ureas, hydroxamic acids, piperazinediones and benzisoxazoles.
Application Notes (PDF Format)
> PL-PBS Resin
PL-PBS Resin is particularly useful in the preparation of a variety of solid supported reagents, particularly via lithiation. It is manufactured directly from the functional monomers. This allows direct control over the loading level and avoids multiple substitution or backbone halogenation when brominating polystyrene resin. The end result is a pure white resin with 100% para substitution.
Application Notes (PDF Format)
> PL-PS/DVB Resin
PL-PS/DVB Resin is manufactured as a base resin for further functionalization and can be used as a scavenger resin for very hydrophobic species in medium polarity solvents such as Dimethylformamide (DMF).
Application Notes (PDF Format)
> PL-REM Resin
PL-REM (Acrylate) resin is an unsaturated ester suitable for the attachment of secondary amines via Michael addition. Quaternization then allows the subsequent cleavage of the resultant tertiary amine by (base catalyzed) Hoffman elimination.
The resin is derived from the PL-CMS copolymer resin to ensure the highest levels of quality and reproducibility.
Application Notes (PDF Format)
> PL-Rink Resin
PL-Rink Resin is typically used for the manufacture of peptide amides, although combinatorial approaches for generation of amides and sulfonamides are also appropriate. The resin is comprised of the Fmoc-protected Rink linker attached directly to a high quality PL-AMS resin. Following deprotection, carboxylic acids may be loaded onto the resultant primary amine group. The corresponding carboxamide can be released by simple treatment with trifluoroacetic acid (TFA).
PL-Rink Resin is sold under license from Aventis.
Application Notes (PDF Format)
> PL-Rink MBHA Resin
PL-Rink MBHA Resin is widely used for the solid phase synthesis of peptide amides using Fmoc chemistry. It is designed to allow the attachment of carboxylic acids, which are subsequently cleaved as amides.
PL-Rink Resin is sold under license from Aventis.
Application Notes (PDF Format)
> PL-SABu Resin, PL-SABz Resin
PL-SABu Resins
PL-SABu is prepared directly by attachment of the sulfamylbutyric acid linker to our own PL-AMS Resin. Carboxylic acids can be coupled to the sulfamyl group of the linker. If the carboxylic acid to be attached contains electron withdrawing groups, the sulfamylbutyryl product should be the resin of choice. The sulfonamide derivative is stable to both basic and nucleophilic reagents until the linker is activated. Diazomethane or iodoacetonitrile can be used to activate the linker so that nucleophilic cleavage can now occur.
PL-SABz Resins
PL-SABz is prepared directly by attachment of the sulfamylbenzoic acid linker to our own PL-AMS Resin resulting in the Kenner-type safety catch linker. Carboxylic acids can be coupled to the sulfamyl group of the linker. If the carboxylic acid to be attached contains electron withdrawing groups, the sulfamylbutyryl product should be the resin of choice. The sulfonamide derivative is stable to both basic and nucleophilic reagents until the linker is activated. Diazomethane or iodoacetonitrile can be used to activatethe linker so that nucleophilic cleavage can now occur.
Application Notes (PDF Format)
Application Notes (PDF Format)
> PL-Wang Resin
PL-Wang is an alkoxybenzylalcohol derivative manufactured from our own PL-CMS resin. This product is designed for acid labile cleavage (using 95% TFA) and is ideally suited to Fmoc protection synthesis strategies.
Application Notes (PDF Format)
> PL-Wang-Acr Resin
Varian, Inc. offers acryloyl Wang (acrylate) resin, suitable for attachment of a variety of amines through a Michael addition reaction. Unlike the related alkenyl resin, PL-REM Resin, Acryloyl Wang resin may be cleaved using TFA to generate peptides with an N-substituted beta amino acid at the C-terminus (ß-peptoids).
This resin has also been used in the generation of cyclic amine species by silver acetate catalysed reaction with imine compounds.
Application Notes (PDF Format)
> PL-Wang-Br Resin
PL-Wang-Br Resin is an activated form of Wang resin, prepared directly from our own Wang resin (see also PL-Wang Resin). Carboxylic acids are readily immobilized on this support as their cesium salt. Amines can also be immobilized on this support and subsequently released as amide or sulfonamide derivatives by reaction with appropriate acids or acid chlorides (see also PL-FMP and PL-FDMP Resin).
Application Notes (PDF Format)
> PL-Wang-TCA Resin
Trichloroacetimidate is a particularly versatile method for activation of Wang resin to allow the immobilization of a variety of species: R-COOH, R-OH, R-SH, etc including less reactive alcohols. The resin can be used to generate a variety of benzyl ether or benzyl ester protected compounds and relies on acid catalysis, making this resin compatible with Fmoc protection.
For example, Fmoc-protected amino acid alcohols (3 equiv) can be loaded on to the resin using dry THF and BF3. Et2O catalyst (0.2 equiv). This allows the facile preparation of a variety of peptides with a C-terminal amino acid alcohol, including octreotide (sandostatin®), a well known peptide drug.
PL-Wang-TCA is advantageous as an alternative to using brominated Wang resins where the halide X leaving group may not be tolerated in the chemistry.
Application Notes (PDF Format)
> PL-Weinreb Resin
PL-Weinreb Resin is produced by attachment of N-Fmoc-N-methoxy-ß-alanine to PL-AMS Resin. Removal of the Fmoc protecting group with piperidine solution is required before attachment of a suitable carboxylic acid to the methoxylamine. This reaction can prove sluggish due to the steric interference of the methoxy group. The resulting Weinreb amide equivalent will generate aldehydes by treatment with LiAlH4.
Application Notes (PDF Format)
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