ChemInform Abstract: Dendritic Molecules on Solid Support: Solid-Phase Synthesis and Applications

Photocleavage from polystyrene beads is a pivotal reaction for solid phase synthesis that relies on photolabile linkers. The photocleavage, usually performed by batch irradiation, suffers from incomplete and slow cleavage. To overcome these issues, continuous flow and high-energy lamps are frequently used, but these setups are hazardous, technically challenging, and expensive. We developed a photocleavage approach that relies on a benchtop LED lamp and magnetic stirring. In this approach, we crush the beads instead of keeping their integrity to increase the yield of photocleavage. This approach proved very efficient for photocleavage of protected oligosaccharides.

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A New Linker for Solid-Phase Synthesis of Oligonucleotides with Terminal Phosphate Group

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20080032 ◽

2008 ◽

Vol 73 (1) ◽

pp. 32-43 ◽

Cited By ~ 2

Author(s):

Ondřej Pačes ◽

Zdeněk Točík ◽

Ivan Rosenberg

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Solid Support ◽

Phosphate Group ◽

Phase Synthesis ◽

Terminal Phosphate Group

Synthesis of a novel cyanoethyl-type linker suitable for the solid-phase synthesis of oligodeoxynucleotides possessing terminal 3'-phosphate group is described. Since the linker is a 2-substituted 2-cyanoethanol, the release of the synthesized oligonucleotide from the solid support is accomplished by β-elimination in the ammonia deprotection step.

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Solid-Phase Traceless Synthesis of Selected Nitrogen-Containing Heterocyclic Compounds. The Encore Technique for Directed Sorting of Modular Solid Support

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20011078 ◽

2001 ◽

Vol 66 (7) ◽

pp. 1078-1106 ◽

Cited By ~ 10

Author(s):

Viktor Krchňák ◽

Jennifer Smith ◽

Josef Vágner

Keyword(s):

Drug Discovery ◽

Hydrogen Atom ◽

Heterocyclic Compounds ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Solid Support ◽

Combinatorial Synthesis ◽

Target Compound ◽

Phase Synthesis ◽

Acidic Reagent

The acid lability of electron-rich N-benzylanilines has been exploited in a linker for the traceless solid-phase synthesis of benzimidazoles, 2-aminobenzimidazoles, quinoxalinones and tetrahydroquinoxalines. The target compound precursors were assembled on a solid-phase support derivatized with either a benzylamine or a benzhydrylamine linker. Exposure to an acidic reagent caused cleavage of the C(benzyl)-N(aniline) bond, releasing the product with only a hydrogen atom on the descending nitrogen. The Encore technique for directed sorting on SynPhase Lanterns has been developed and applied to combinatorial synthesis of generic drug discovery libraries.

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Solid-phase synthesis and fluorine-18 radiolabeling of cycloRGDyK

Organic & Biomolecular Chemistry ◽

10.1039/c6ob01636g ◽

2016 ◽

Vol 14 (37) ◽

pp. 8659-8663 ◽

Cited By ~ 5

Author(s):

Ryan A. Davis ◽

Kevin Lau ◽

Sven H. Hausner ◽

Julie L. Sutcliffe

Keyword(s):

Peptide Synthesis ◽

High Purity ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Continuous Process ◽

Solid Support ◽

Purification Step ◽

Phase Synthesis

A rapid, efficient single continuous process for peptide synthesis, cyclization, and radiolabeling on solid-support with a single purification step afforded a high purity radiotracer.

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3-(Tributylstannyl)allyl Alcohols: Useful Building Blocks for Solid-Phase Synthesis of Skipped Dienes and Trienes

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20000434 ◽

2000 ◽

Vol 65 (3) ◽

pp. 434-454 ◽

Cited By ~ 3

Author(s):

Miroslav Havránek ◽

Dalimil Dvořák

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Building Blocks ◽

Solid Support ◽

Stille Coupling ◽

Phase Synthesis ◽

Negative Results ◽

Allyl Alcohols

Repeated Stille coupling of 3-substituted 3-(tributylstannyl)allyl alcohols 2 on a solid support was used to synthesize a 21 × 21 library of skipped dienes and a 21 × 21 × 21 library of skipped trienes. Starting 3-(tributylstannyl)allyl alcohols were prepared by Pd-catalyzed hydrostannation of substituted prop-2-yn-1-ols, by hydroalumination by LiAlH4 followed with transmetallation to tin using tributyltin methoxide, or by substitution of chlorine in (Z)-6-chloro-3-(tributylstannyl)hex-2-en-1-ol with appropriate nucleophile. Synthesized libraries were tested for the activity to endorphin receptors, but with negative results.

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Microwave assisted solid-phase synthesis of substituted tetraazaporphyrins and a phthalocyanine-peptide conjugate

Journal of Porphyrins and Phthalocyanines ◽

10.1142/s1088424610002744 ◽

2010 ◽

Vol 14 (10) ◽

pp. 891-903 ◽

Cited By ~ 4

Author(s):

Mercy Mudyiwa ◽

Margaret W. Ndinguri ◽

Steven A. Soper ◽

Robert P. Hammer

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Synthesis Method ◽

Reaction Times ◽

Solid Support ◽

Phase Synthesis ◽

Covalently Bonded ◽

Poly Ethylene ◽

High Degree ◽

Acid Labile

Various asymmetrically substituted phthalocyanines (Pcs) and porphyrazines (Pzs) have been synthesized in good yields using a solid-phase synthesis method with a poly(ethylene glycol) (PEG) resin attached to an indole linker as the solid support. These compounds are formed by cross condensation of maleonitrile or phthalonitrile with another phthalonitrile covalently bonded to the solid support with an amino linking group. The polymer bound Pc or Pz is separated by filtration, and washing the symmetrical Pc or Pz by-product. The amine Pc -appended to polyethylene glycol resin is further reacted to yield azide whilst still on the solid support. Cleavage of the Pc or Pz off the solid support results in 3:1 asymmetric Pz or Pz with high degree of purity, requiring minimal further purification. The use of hydrophilic PEG-based resin allows the symmetrical compound to be removed completely by washing whereas the acid labile indole linker makes it easier to cleave the product under mild conditions. The conjugation abilities of these compounds have been demonstrated by the successful conjugation of one of the azide Pcs with a peptide elaborated with an alkyne function. Use of microwave for the synthesis of these compounds results in shorter reaction times, higher yields and higher degree of purity.

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Solid-Phase Synthesis of 1,3,7,8-Tetrasubstituted Xanthine Derivatives on Traceless Solid Support

ACS Combinatorial Science ◽

10.1021/acscombsci.5b00148 ◽

2015 ◽

Vol 18 (1) ◽

pp. 70-74 ◽

Cited By ~ 9

Author(s):

Doohyun Lee ◽

Seungyeon Lee ◽

Kwang-Hyeon Liu ◽

Jong-Sup Bae ◽

Dong Jae Baek ◽

...

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Solid Support ◽

Phase Synthesis ◽

Xanthine Derivatives

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A Different Approach to the EGFR Inhibitor Gefitinib Involving Solid-Phase Synthesis

Synlett ◽

10.1055/s-0037-1610127 ◽

2018 ◽

Vol 29 (10) ◽

pp. 1346-1350 ◽

Cited By ~ 2

Author(s):

Luísa Carvalho ◽

André Sequeira ◽

Ana Lourenço ◽

Luísa Ferreira ◽

Paula Branco ◽

...

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Solid Support ◽

Egfr Inhibitor ◽

Phase Synthesis ◽

Synthetic Strategy ◽

Colorimetric Assays ◽

First Time ◽

Synthesis Approach

An efficient solid-phase synthesis approach is here reported for the first time to prepare the EGFR inhibitor Gefitinib. The five-step synthetic strategy used FMP resin as the solid support, and FTIR and colorimetric assays were used to track the reaction’s progress. Gefitinib was obtained with an overall yield of 40%.

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Facile one-step solid-phase synthesis of multitopic organic–DNA hybrids via “click” chemistry

Chemical Science ◽

10.1039/c3sc53206b ◽

2014 ◽

Vol 5 (3) ◽

pp. 1091-1096 ◽

Cited By ~ 40

Author(s):

Ryan V. Thaner ◽

Ibrahim Eryazici ◽

Omar K. Farha ◽

Chad A. Mirkin ◽

SonBinh T. Nguyen

Keyword(s):

Click Chemistry ◽

Small Molecule ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Solid Support ◽

One Pot ◽

Phase Synthesis ◽

One Step

Small molecule–DNA hybrids can be synthesized in a one-pot fashion and in good yields by coupling multiazide cores to alkyne-modified DNAs on a solid support using click chemistry.

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