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T1 - The solid-phase combinatorial synthesis of β-thioketones

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T1 - Solid-Phase Synthesis of an Isoxazolinopyrrole Library

AB - A solid phase traceless synthesis of 2-arylaminobenzimidazoles in three combinatorial steps is reported that is based on acid lability of N-benzylanilines. MBHA resin was reacted with o-nitrobenzenes, the nitro group was reduced by tin(II) chloride, the resin-bound o-phenylene diamine was treated with isothiocyanates, and the resulting thiourea cyclized by carbodiimide. 2-Arylaminobenzimidazoles were further derivatized with alkyl halides. Target compounds were cleaved from the solid support by TFA or gaseous HF.

T1 - A solid phase traceless synthesis of 2-arylaminobenzimidazoles
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The first linking group used for peptide synthesis bears the name of the father of solid phase synthesis. Merrifield resin is cross-linked polystyrene functionalised with a chloromethyl group. The carbonyl group is attached by the nucleophilic displacement of the chloride with a caesium carboxylate salt in DMF. Cleavage to regenerate the carboxylic acid is usually achieved by hydrogen fluoride. (Figure 7)

Solid-phase synthesis - Wikipedia

nucleic acid chemistry; oligonucleotides; solid‐phase synthesis; molecular biology
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John D. Wade and Yuji Nishiuchi
Co-Chairs 6th Modern Solid Phase Peptide Synthesis & Its Applications Symposium

Utilizing polymer-bound anthranilic acid derivatives, we were able to obtain 4-hydroxyquinolin-2(1H)-ones in 50-99% five-or six-step overall yields and 65-95% purities through the adaptation of a Dieckmann-type condensation reaction to a C-C bond-forming cyclative cleavage step. The reactions on solid phase were monitored by on-bead ATR-FTIR spectroscopic methods, colorimetric tests, and/or cleavage experiments.

Solid Phase Synthesis - Solid-Phase Combinatorial Chemistry

T1 - Novel solid-phase synthetic method for combinatorial generation of a 4-hydroxyquinolin-2(1H)-one-based library
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Merrifield developed a series of chemical reactions that can be used to synthesise proteins. The direction of synthesis is opposite to that used in the cell. The intended carboxy terminal amino acid is anchored to a solid support. Then, the next amino acid is coupled to the first one. In order to prevent further chain growth at this point, the amino acid, which is added, has its amino group blocked. After the coupling step, the block is removed from the primary amino group and the coupling reaction is repeated with the next amino acid. The process continues until the peptide or protein is completed. Then, the molecule is cleaved from the solid support and any groups protecting amino acid side chains are removed. Finally, the peptide or protein is purified to remove partial products and products containing errors.

In solid phase support synthesis, the solid support is generally based on a polystyrene resin. The most commonly used resin supports for SPS include spherical beads of lightly cross linked gel type polystyrene (1–2% divinylbenzene) and poly(styrene-oxyethylene) graft copolymers which are functionalised to allow attachment of linkers and substrate molecules. Each of these materials has advantages and disadvantages depending on the particular application. (5, 6, 7)

KW - Solid-phase synthesis
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  • Solid phase and combinatorial synthesis of compounds …

    The combinatorial "split-mix synthesis" is based on the solid phase synthesis developed by Merrifield

  • Solid phase-combinatorial chemistry to prepare

    08/01/2010 · Highlights in the solid-phase organic synthesis of natural products and analogues

  • Solid phase combinatorial synthesis of a xanthone …

    03/11/2000 · Solid-Phase Oligosaccharide Synthesis and Combinatorial ..

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Solid-phase oligonucleotide synthesis - ATDBio

Peter H. Seeberger received his B.S. degree in 1989 from the Universität Erlangen-Nürnberg, where he studied chemistry as a Bavarian government fellow. In 1990 he moved as a Fulbright Scholar to the University of Colorado, where he earned his Ph.D. degree in Biochemistry under the guidance of Marvin H. Caruthers in 1995. After a postdoctoral fellowship with Samuel J. Danishefsky at the Sloan-Kettering Institute for Cancer Research in New York City, he began his independent career at the Massachusetts Institute of Technology in January 1998. Since 1999 he has been the Firmenich Assistant Professor of Chemistry. His research interests focus on the interface of chemistry and biology and in particular on the role of complex carbohydrates and glycoconjugates in information transfer in biological systems. His group has developed new methods for the automated solid-phase synthesis of complex carbohydrates and glycosaminoglycans that serve as molecular tools. Other interests include synthetic methodology, total synthesis, immunology, and biochemical and biophysical studies of carbohydrates.

Optimization Of Solid Phase Combinatorial Synthesis

AB - Utilizing polymer-bound anthranilic acid derivatives, we were able to obtain 4-hydroxyquinolin-2(1H)-ones in 50-99% five-or six-step overall yields and 65-95% purities through the adaptation of a Dieckmann-type condensation reaction to a C-C bond-forming cyclative cleavage step. The reactions on solid phase were monitored by on-bead ATR-FTIR spectroscopic methods, colorimetric tests, and/or cleavage experiments.

SOLID-PHASE SYNTHESIS: FROM REVOLUTION TO …

N2 - Utilizing polymer-bound anthranilic acid derivatives, we were able to obtain 4-hydroxyquinolin-2(1H)-ones in 50-99% five-or six-step overall yields and 65-95% purities through the adaptation of a Dieckmann-type condensation reaction to a C-C bond-forming cyclative cleavage step. The reactions on solid phase were monitored by on-bead ATR-FTIR spectroscopic methods, colorimetric tests, and/or cleavage experiments.

Optimization of solid-phase combinatorial synthesis …

Continued and exciting advances in all aspects of the science of solid phase peptide synthesis, ranging from solid supports, instrumentation, chemistries and protocols, have allowed the acquisition of ever more complex and large biological targets. These include small proteins, de novo designed peptides with purposely conferred structural properties, cyclic peptides, post-translationally modified peptides and peptide-oligonucleotide conjugates. Importantly, these advances that have allowed access to this diverse array of peptide products have enabled a dramatic increase in the chemical, biological and medical applications of peptides.

This symposium provides a superb opportunity for all practitioners (and interested observers!) of solid phase peptide synthesis together with those who use synthetic peptides for a myriad of applications to gather at Fraser Island to discuss the latest developments over two and a half relaxed and convivial days.

Topics will include:

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