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Synthesis Make me a molecule Chemistry Biology Materials.

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Presentation on theme: "Synthesis Make me a molecule Chemistry Biology Materials."— Presentation transcript:

1 Synthesis Make me a molecule Chemistry Biology Materials

2 DNA, Genes, and Proteins

3 Genomics, Proteomics and Chemical Genetics
Control Biological Functions Genomics Gene Sequence: ~30,000 genes - unable to identify therapeutic targets no protein function and disease relevance Drug Discovery Proteomics Chemical Genetics Protein Function: - purification and structure determination - ~100,000 proteins in human - 75% no known cellular functions Small Molecules: - modulate biological functions of proteins

4 Protein Function (Drug Action)
normal signal protein activate protein function false signal deactivate protein function

5 Selected Medications of 20th Century

6 Selected Medications of 20th Century

7 Target-Oriented Organic Synthesis
Known active sites of target proteins Design and synthesis of target molecules biological effects

8 Library of diverse small molecules
Diversity-Oriented Organic Synthesis unknown proteins 이상 Library of diverse small molecules 정상

9 Combinatorial Chemistry

10 Combinatorial Library
• 4 개의 monomer Nn Combinations 44 = 256개 tetramer

11 Solid Phase Synthesis의 기본원리
resin + monomer shake wash resin cleavage wash

12 Solid-Phase Synthesis of Peptides
In 1960s, Bruce Merrifield: peptide synthesis from amino acids polymer bead amino acid cleave peptide

13 Solid Phase Library Synthesis
• polymer supported synthesis: easy purification • fast generation of diverse library of molecules in few steps • limited reactions compared to solution reactions Split-Mix (split-pool) synthesis Parallel synthesis

14 Split-Mix Process tag each bead! 33= 27 Mix-Split Couple Mix-Split

15 Parallel synthesis - no tagging beads!
- synthesis of small number of focused library

16 Solid Phase Library In 1991s, Houghten & Lam: synthesis of a huge peptide library 20 amino acids Solid-phase synthesis 202 = 400 dipeptides DNA: fully automatic (solution) peptide 203 = 8000 tripeptides carbohydrate small molecule (drug-like) 204 = 160,000 tetrapeptides ln 1992, Jon Ellman: synthesis of non-peptide drug-like molecules by solid phase synthesis

17 Combination of Chemical Building Blocks
2,180,106 compounds

18 Virtual Library virtual library: computer simulated fitting of virtual molecules with the active site of the target enzyme Novel compounds that bind to enzymes or receptors can be discovered by finding two fragments that bind and then synthetically combining

19 Applications of Combinatorial Chemistry
Chemical biology: diversity-oriented synthesis of small organic molecules Pharmaceutical industry: rapid synthesis of a huge number of drug-like molecules Material science: new approach for the discovery of new materials Catalyst discovery: fast discovery of new catalysts

20 Supramolecular Chemistry

21 1. Molecular chemistry- Covalent bond
urea 150 years ago palytoxin

22 초분자 화학 2. Supramolecular chemistry- Chemistry beyond molecules
Assembly of molecules – Molecular recognition Non-covalent bonds: - electrostatic forces - hydrogen bonds - van der Waals interactions - dipole interactions - hydrophobic interactions, etc 1987 노벨화학상: 초분자화학 Charles Pedersen, Jean-Marie Lehn, and Donald J. Cram

23 DNA and Hydrogen Bonds

24 DNA and Hydrogen Bonds Which pair forms stronger hydrogen bonds? And Why?

25 DNA and Hydrogen Bonds

26 New Materials Based on Hydrogen Bonds

27 Crown Ethers 18-crown-6 15-crown-5

28 Preorganized Ionophores
Preorganization: both binding affinity and selectivity are considerably increased W.C. Still D.J. Cram

29 Anion Recognition

30 Anion Recognition

31 Chemosensors Signals: - fluorescence - color - electric signal...

32 Chemosensors 1 only Hg2+ Ag+ Cu2+ Cd2+ Pb2+ Zn2+

33 Carcerand

34 Molecular Machine

35 생체 분자기계 Linear movement - muscle
(myosin moving along an actin filament) ATP Synthase Bacterial Flagellar Motor

36 Interlocked Molecules
Rotaxane Rota (wheel) + axis (axle) Catenane Catena (chain)

37 분자 셔틀 버스 이동

38 인공 분자기계 A catenane-based switching device for electric circuits.

39 인공 분자기계 Catenane-based molecular rotor. A unidirectional rotation of the small rings along the large ring is achieved by their sequential complexation and decomplexation with four station parts A-D on exposure to light, heat, and chemical stimuli.

40 분자 근육

41 분자 엘리베이터

42 분자 가위

43 인공 분자기계 Chiral molecular motor composed of a tetrasubstituted alkene. Photoinduced and thermal-induced unidirectional rotation.

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