Sijbren Otto

ORCID: 0000-0003-0259-5637
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About
Contact & Profiles
Research Areas
  • Chemical Synthesis and Analysis
  • Supramolecular Chemistry and Complexes
  • Origins and Evolution of Life
  • Photoreceptor and optogenetics research
  • Supramolecular Self-Assembly in Materials
  • Molecular Sensors and Ion Detection
  • Mass Spectrometry Techniques and Applications
  • Analytical Chemistry and Chromatography
  • Protein Structure and Dynamics
  • DNA and Biological Computing
  • Gene Regulatory Network Analysis
  • Asymmetric Synthesis and Catalysis
  • Synthetic Organic Chemistry Methods
  • Evolution and Genetic Dynamics
  • Surface Chemistry and Catalysis
  • Photosynthetic Processes and Mechanisms
  • Molecular Junctions and Nanostructures
  • Microbial Metabolic Engineering and Bioproduction
  • History and advancements in chemistry
  • Various Chemistry Research Topics
  • Click Chemistry and Applications
  • Modular Robots and Swarm Intelligence
  • Advanced biosensing and bioanalysis techniques
  • Crystallization and Solubility Studies
  • Lipid Membrane Structure and Behavior

University of Groningen
2016-2025

Centre for Structural Systems Biology
2014-2015

Dialyse Centrum Groningen
2014-2015

Wageningen University & Research
2015

University of Cambridge
2000-2012

University of Strathclyde
2008

University of Kaiserslautern
2006

Chulalongkorn University
2006

Heinrich Heine University Düsseldorf
2003

National University of Rosario
2002

At Sixes and Sevens Molecular synthesis macroscopic aggregation have often been regarded as entirely separate processes. From the researcher's standpoint, once reagents mixed, is largely passive, whereas processes such crystallization can be more actively manipulated. Carnall et al. (p. 1502 ) characterized an unusual system in which formation of aggregated cyclic macromolecules (macrocycles) from small peptide-based building blocks was governed by intimately interdependent factors ranging...

10.1126/science.1182767 article EN Science 2010-03-18

Dynamic combinatorial chemistry (DCC) is a subset of where the library members interconvert continuously by exchanging building blocks with each other. libraries (DCLs) are powerful tools for discovering unexpected and have given rise to many fascinating molecules, ranging from interlocked structures self-replicators. Furthermore, dynamic molecular networks can produce emergent properties at systems level, which provide exciting new opportunities in chemistry. In this perspective we will...

10.1021/ja402586c article EN Journal of the American Chemical Society 2013-06-03

We have discovered two receptors for different guests from a single dynamic combinatorial library. Each of the amplifies formation tightly binding host at expense unfit library members. Small differences in host-guest translate into useful amplification. The selected hosts could be readily synthesized using biased libraries that contain only right ratio those building blocks were by guests. These results establish chemistry as practical method not discovery but also synthesis new receptors.

10.1126/science.1072361 article EN Science 2002-07-26

This perspective describes how kinetic studies of organic reactions can be used to increase our understanding hydrophobic interactions. In turn, interactions as a tool influence chemical reactions.

10.1039/b305672d article EN Organic & Biomolecular Chemistry 2003-01-01

Directed chemical synthesis can produce a vast range of molecular structures, but the intended product must be known at outset. In contrast, evolution in nature lead to efficient receptors and catalysts whose structures defy prediction. To access such unpredictable we prepared dynamic combinatorial libraries which reversibly binding building blocks assemble around receptor target. We selected for an acetylcholine by adding neurotransmitter solutions dipeptide hydrazones...

10.1126/science.1109999 article EN Science 2005-03-11

ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTDynamic Combinatorial Libraries of Macrocyclic Disulfides in WaterSijbren Otto, Ricardo L. E. Furlan, and Jeremy K. M. SandersView Author Information University Cambridge, Department Chemistry Lensfield Road, Cambridge CB2 1EW, UK Cite this: J. Am. Chem. Soc. 2000, 122, 48, 12063–12064Publication Date (Web):November 16, 2000Publication History Received3 August 2000Published online16 November inissue 1 December...

10.1021/ja005507o article EN Journal of the American Chemical Society 2000-11-16

Abstract This review illustrates how water, as an environmentally friendly solvent, can have significant additional benefits when it is used a solvent for the Diels_Alder reaction. The mechanism by which unique properties of water enhance rate and selectivity are discussed. Also, possibilities achievement further increases in enantioselectivity aqueous reactions through Lewis-acid micellar catalysis reviewed.

10.1351/pac200072071365 article EN Pure and Applied Chemistry 2000-01-01

Here we report the first detailed study of a Diels−Alder (DA) reaction that is catalyzed by Lewis acids in water. The effect Co2+, Ni2+, Cu2+ and Zn2+ ions as acid catalysts on rate endo−exo selectivity DA between bidentate dienophiles 3-phenyl-1-(2-pyridyl)-2-propen-1-ones (1a−e) cyclopentadiene (2) water has been studied. Relative to uncatalyzed acetonitrile, catalysis 0.010 M Cu(NO3)2 accelerates factor 79 300. kinetics were analyzed terms equilibrium constants for complexation with 1a−e...

10.1021/ja960318k article EN Journal of the American Chemical Society 1996-01-01

Combinatorial chemistry is a tool for selecting molecules with special properties. Dynamic combinatorial started off aiming to be just that. However, unlike ordinary chemistry, the interconnectedness of dynamic libraries gives them an extra dimension. An understanding these molecular networks at systems level essential their use as selection and creates exciting new opportunities in chemistry. In this feature article we discuss selected examples considerations related advanced exploitation...

10.1039/c0cc03759a article EN Chemical Communications 2010-11-29

A dynamic combinatorial library of potential anion receptors was generated from a cyclic peptide disulfide dimer and series dithiol spacers. Exposing the to KI or K2SO4 led amplification two new neutral that bind anions through hydrogen bonding with up micromolar affinity in aqueous solution. Thermodynamic studies suggest these second-generation outclass previously described first-generation receptor, largely as result more favorable enthalpy binding. These results demonstrate optimization...

10.1021/ja0351589 article EN Journal of the American Chemical Society 2003-06-05

Abstract Self-replicating molecules are likely to have played a central role in the origin of life. Most scenarios Darwinian evolution at molecular level require self-replicators capable exponential growth, yet only very few replicators been reported date and general design criteria for replication lacking. Here we show that peptide-functionalized macrocyclic self-replicator exhibits growth when subjected mild agitation. The replicator self-assembles into elongated fibres which ends promote...

10.1038/ncomms8427 article EN cc-by Nature Communications 2015-06-17

Abstract Directing self‐assembly processes out‐of‐equilibrium to yield kinetically trapped materials with well‐defined dimensions remains a considerable challenge. Kinetically controlled assembly of self‐synthesizing peptide‐functionalized macrocycles through nucleation–growth mechanism is reported. Spontaneous fiber formation in this system effectively shut down as most the material diverted into metastable non‐assembling trimeric and tetrameric macrocycles. However, upon adding seeds...

10.1002/anie.201501965 article EN Angewandte Chemie International Edition 2015-05-27

Dynamic combinatorial libraries (DCLs) are molecular networks in which the network members exchange building blocks. The resulting product distribution is initially under thermodynamic control. Addition of a guest or template molecule tends to shift equilibrium towards compounds that receptors for guest.This Account gives an overview our work this area. We have demonstrated template-induced amplification synthetic receptors, has given rise several high-affinity binders cationic and anionic...

10.1021/ar200246j article EN Accounts of Chemical Research 2012-01-20

Stacks of macrocycles, assembled using reversible disulfide-bond formation, are covalently captured by photoinitiated exchange disulfide bonds, inducing the formation hydrogels (see picture). This strategy allows access to structures beyond thermodynamic minima traditionally targeted dynamic combinatorial chemistry.

10.1002/anie.201103297 article EN Angewandte Chemie International Edition 2011-07-14

A family of self-replicating macrocycles was developed using dynamic combinatorial chemistry. Replication is driven by self-assembly the replicators into fibrils and relies critically on mechanically induced fibril fragmentation. Analysis separate libraries made from one six peptide-functionalized building blocks different hydrophobicity revealed two selection criteria that govern emergence these systems. First, need to have a critical macrocycle size endows them with sufficient multivalency...

10.1021/ja4067805 article EN Journal of the American Chemical Society 2013-11-12
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