Carbohydrates as versatile platforms in the construction of small compound libraries

2005 ◽  
Vol 77 (7) ◽  
pp. 1173-1181 ◽  
Author(s):  
Mattie S. M. Timmer ◽  
Steven H. L. Verhelst ◽  
Gijsbert M. Grotenbreg ◽  
Mark Overhand ◽  
Herman S. Overkleeft
Keyword(s):  
Antibacterial Activity ◽  
Solid Phase ◽  
Building Blocks ◽  
Peptide Mimetics ◽  
Carbohydrate Chemistry ◽  
Ring Closing Metathesis ◽  
Rapid Synthesis ◽  
Small Compound ◽  
Compound Libraries ◽  
Three Component Reaction

This paper presents our recent results concerning the use of carbohydrates as cheap, chiral, and enantiopure starting materials in the construction of a variety of densely functionalized molecules. The compatibility of ring-closing metathesis with standard carbohydrate chemistry is demonstrated in the synthesis of new stereoisomers of deoxystreptamine and neamine–important building blocks for the generation of synthetic aminoglycosides with potential antibacterial activity. Ring-closing metathesis is also a key step in the rapid synthesis of new indolizidines and quinolizidines, and in a new solid-phase assisted carbohydrate-based combinatorial scaffold strategy. Further, some of our latest results in the conformational analysis of sugar amino acid-based peptide mimetics and in the development of a novel Ugi-type three-component reaction of sugar-derived azido-aldehydes are discussed.

Solid- and solution-phase synthesis of bioactive dihydropyrimidines

2004 ◽  
Vol 76 (5) ◽  
pp. 1017-1024 ◽  
Author(s):  
Doris Dallinger ◽  
A. Stadler ◽  
C. O. Kappe
Keyword(s):  
High Throughput ◽  
High Throughput Screening ◽  
Multicomponent Reactions ◽  
Solid Phase ◽  
Cost Effective ◽  
Phase Synthesis ◽  
Compound Libraries ◽  
Effective Manner ◽  
Three Component Reaction ◽  
Solution Phase Synthesis

With the emergence of high-throughput screening in the pharmaceutical industry over a decade ago, synthetic chemists were faced with the challenge of preparing large collections of molecules to satisfy the demand for new screening compounds. The unique exploratory power of multicomponent reactions such as the Biginelli three-component reaction was soon recognized to be extremely valuable to produce compound libraries in a time- and cost-effective manner. The present review summarizes synthetic advances from our laboratories for the construction of Biginelli libraries via solution-and solid-phase strategies that are amenable to a high-throughput or combinatorial format.

Modified Solid-Phase Methods for the Rapid Synthesis of Opioid Peptides

1991 ◽  
Author(s):  
Richard A. Houghten ◽  
◽  
John M. Ostresh ◽  
Suzanne M. Pratt
Keyword(s):  
Opioid Peptides ◽  
Solid Phase ◽  
Rapid Synthesis

Development of Strategies for Glycopeptide Synthesis: An Overview on the Glycosidic Linkage

2020 ◽  
Vol 24 (21) ◽  
pp. 2475-2497
Author(s):  
Andrea Verónica Rodríguez-Mayor ◽  
German Jesid Peralta-Camacho ◽  
Karen Johanna Cárdenas-Martínez ◽  
Javier Eduardo García-Castañeda
Keyword(s):  
Chemical Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Heterogeneous Environments ◽  
Phase Synthesis ◽  
Low Concentrations ◽  
Biological Sources ◽  
Synthetic Routes ◽  
The Impact ◽  
Potential Use

Glycoproteins and glycopeptides are an interesting focus of research, because of their potential use as therapeutic agents, since they are related to carbohydrate-carbohydrate, carbohydrate-protein, and carbohydrate-lipid interactions, which are commonly involved in biological processes. It has been established that natural glycoconjugates could be an important source of templates for the design and development of molecules with therapeutic applications. However, isolating large quantities of glycoconjugates from biological sources with the required purity is extremely complex, because these molecules are found in heterogeneous environments and in very low concentrations. As an alternative to solving this problem, the chemical synthesis of glycoconjugates has been developed. In this context, several methods for the synthesis of glycopeptides in solution and/or solid-phase have been reported. In most of these methods, glycosylated amino acid derivatives are used as building blocks for both solution and solid-phase synthesis. The synthetic viability of glycoconjugates is a critical parameter for allowing their use as drugs to mitigate the impact of microbial resistance and/or cancer. However, the chemical synthesis of glycoconjugates is a challenge, because these molecules possess multiple reaction sites and have a very specific stereochemistry. Therefore, it is necessary to design and implement synthetic routes, which may involve various protection schemes but can be stereoselective, environmentally friendly, and high-yielding. This review focuses on glycopeptide synthesis by recapitulating the progress made over the last 15 years.

Fully Automated Parallel Oligonucleotide Synthesizer

2001 ◽  
Vol 66 (8) ◽  
pp. 1299-1314 ◽  
Author(s):  
Michal Lebl ◽  
Christine Burger ◽  
Brett Ellman ◽  
David Heiner ◽  
Georges Ibrahim ◽  
...  
Keyword(s):  
Solid Phase ◽  
Building Blocks ◽  
Solid Support ◽  
Continuous Operation ◽  
Gear Pump ◽  
Oligonucleotide Synthesis ◽  
Center Of Rotation ◽  
Microtiter Plates ◽  
The Individual ◽  
Design And Construction

Design and construction of automated synthesizers using the tilted plate centrifugation technology is described. Wash solutions and reagents common to all synthesized species are delivered automatically through a 96-channel distributor connected to a gear pump through two four-port selector valves. Building blocks and other specific reagents are delivered automatically through banks of solenoid valves, positioned over the individual wells of the microtiterplate. These instruments have the following capabilities: Parallel solid-phase oligonucleotide synthesis in the wells of polypropylene microtiter plates, which are slightly tilted down towards the center of rotation, thus generating a pocket in each well, in which the solid support is collected during centrifugation, while the liquid is expelled from the wells. Eight microtiterplates are processed simultaneously, providing thus a synthesizer with a capacity of 768 parallel syntheses. The instruments are capable of unattended continuous operation, providing thus a capacity of over two millions 20-mer oligonucleotides in a year.

scholarly journals Synthesis and Self-assembly of Amphiphilic Precision Glycomacromolecules

2021 ◽  
Author(s):  
Alexander Banger ◽  
Julian Sindram ◽  
Marius Otten ◽  
Jessica Kania ◽  
Alexander Strzelczyk ◽  
...  
Keyword(s):  
Self Assembly ◽  
Solid Phase ◽  
Building Blocks ◽  
Polymer Synthesis

We present the synthesis of so called amphiphilic glycomacromolecules (APGs) by using solid-phase polymer synthesis. Based on tailor made building blocks, monosdisperse APGs with varying compositions are synthesized, introducing carbohydrate...

ChemInform Abstract: Modified Solid-Phase Methods for the Rapid Synthesis of Opioid Peptides

ChemInform ◽  
2010 ◽  
Vol 24 (27) ◽  
pp. no-no ◽  
Author(s):  
R. A. HOUGHTEN ◽  
J. M. OSTRESH ◽  
S. M. PRATT
Keyword(s):  
Opioid Peptides ◽  
Solid Phase ◽  
Rapid Synthesis

A New Strategy for Solid-Phase Depsipeptide Synthesis Using Recoverable Building Blocks

2005 ◽  
Vol 7 (4) ◽  
pp. 597-600 ◽  
Author(s):  
Fernando Albericio ◽  
Klaus Burger ◽  
Javier Ruíz-Rodríguez ◽  
Jan Spengler
Keyword(s):  
Solid Phase ◽  
Building Blocks ◽  
New Strategy
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