In XNA Nucleotides. the Deoxyribose and Ribose Sugar Groups of DNA
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Peptide Nucleic Acids, Morpholinos and Related Antisense Biomolecules
MEDICAL INTELLIGENCE UNIT Peptide Nucleic Acids, Morpholinos and Related Antisense Biomolecules Christopher G. Janson, M.D. Departments of Neurosurgery, Neurology and Molecular Genetics Cell and Gene Therapy Center UMDNJ-Robert Wood Johnson Medical School Camden, New Jersey, U.S.A. Matthew J. During, M.D., ScD. Department of Molecular Medicine and Pathology University of Auckland Auckland, New Zealand LANDES BIOSCIENCE / EUREKAH.COM KLUWER ACADEMIC / PLENUM PUBLISHERS GEORGETOWN, TEXAS NEW YORK, NEW YORK USA U.SA PEPTIDE NUCLEIC ACIDS, MORPHOLINOS AND RELATED ANTISENSE BIOMOLECULES Medical Intelligence Unit Landes Bioscience / Eurekah.com Kluwer Academic / Plenum Publishers Copyright ©2006 Eurekah.com and Kluwer Academic / Plenum Publishers All rights reserved. No part of this book may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopy, recording, or any information storage and retrieval system, without permission in writing from the publisher, vdth the exception of any material supplied specifically for the purpose of being entered and executed on a computer system; for exclusive use by the Purchaser of the work. Printed in the U.S.A. Kluwer Academic / Plenum PubHshers, 233 Spring Street, New York, New York, U.S.A. 10013 http ://www.wkap .nl/ Please address all inquiries to the Publishers: Landes Bioscience / Eurekah.com, 810 South Church Street, Georgetown, Texas, U.S.A. 78626 Phone: 512/ 863 7762; FAX: 512/ 863 0081 http ://v^^ww.eurekah. com http://www.landesbioscience.com Peptide -
(12) Patent Application Publication (10) Pub. No.: US 2013/0203610 A1 Meller Et Al
US 20130203610A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2013/0203610 A1 Meller et al. (43) Pub. Date: Aug. 8, 2013 (54) TOOLS AND METHOD FOR NANOPORES Related U.S. Application Data UNZIPPING-DEPENDENT NUCLECACID (60) Provisional application No. 61/318,872, filed on Mar. SEQUENCING 30, 2010. (75) Inventors: Amit Meller, Brookline, MA (US); Alon Publication Classification Singer, Brighton, MA (US) (51) Int. Cl. (73) Assignee: TRUSTEES OF BOSTON CI2O I/68 (2006.01) UNIVERSITY, Boston, MA (US) (52) U.S. Cl. CPC .................................... CI2O I/6874 (2013.01) (21) Appl. No.: 13/638,455 USPC ................................................. 506/6:506/16 (57) ABSTRACT (22) PCT Filed: Mar. 30, 2011 Provided herein is a library that comprises a plurality of molecular beacons (MBs), each MB having a detectable (86). PCT No.: PCT/US2O11AO3O430 label, a detectable label blocker and a modifier group. The S371 (c)(1), library is used in conjunction with nanopore unzipping-de (2), (4) Date: Apr. 17, 2013 pendent sequencing of nucleic acids. Patent Application Publication Aug. 8, 2013 Sheet 1 of 18 US 2013/020361.0 A1 . N s Patent Application Publication Aug. 8, 2013 Sheet 2 of 18 US 2013/020361.0 A1 I’9IAI ::::::::::: Dº3.modoueN Patent Application Publication Aug. 8, 2013 Sheet 3 of 18 US 2013/020361.0 A1 Z’9IAI ~~~~~~~~~);........ Patent Application Publication Aug. 8, 2013 Sheet 4 of 18 US 2013/020361.0 A1 s :·.{-zzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzz iii. 9 iii.338 lii &S Patent Application Publication Aug. 8, 2013 Sheet 5 of 18 US 2013/020361.0 A1 s r Patent Application Publication Aug. -
Peptide Analogue of Glycol Nucleic Acid†
Communications to the Editor Bull. Korean Chem. Soc. 2011, Vol. 32, No. 8 2863 DOI 10.5012/bkcs.2011.32.8.2863 γ3PNA: Peptide Analogue of Glycol Nucleic Acid† Taedong Ok, Joohee Lee, and Hee-Seung Lee* Molecular-Level Interface Research Center, Department of Chemistry, KAIST, Daejeon 305-701 *E-mail: [email protected] Received February 7, 2011, Accepted February 9, 2011 Key Words : Peptide nucleic acids, GNA In the research of the chemical etiology of nucleic acid chemical yield were obtained with Mmt for γ3C and γ3G, Boc structure, the studies from Eschenmoser group1 and Nielsen for γ3A, respectively. In addition, the order of reactions at the group2 have demonstrated that the Watson-Crick base pairing initial steps turned out to be important for efficient synthesis. can be supported by various backbone derivatives. Inspired by For example, in case of γ3C, the protection of the amino groups the groundbreaking results, other researchers have devoted should be prior to the substitution reaction, whereas the other their attention to finding artificial nucleic acids that can form route worked better for the purine monomers (γ3A and γ3G). duplexes, in which both synthetic accessibility and new The detailed synthetic procedures are summarized in characteristics for potential therapeutic (or diagnostic) use are Scheme 1. The common intermediate bromide 1 was easily desirable aims.3 In this context, GNA (glycol nucleic acid, prepared from (S)-epichlorohydrin (> 99%ee) in three steps Figure 1A) is a promising artificial nucleic acid because it is (34% overall yield).6,7 For the synthesis of γ3A, the bromide 1 structurally very simple with a high atom economy and was reacted with unprotected adenine base in the presence of forms a duplex by Watson-Crick base pairing.4 sodium hydride in DMF for 48 hr at room temperature. -
Chapter 23 Nucleic Acids
7-9/99 Neuman Chapter 23 Chapter 23 Nucleic Acids from Organic Chemistry by Robert C. Neuman, Jr. Professor of Chemistry, emeritus University of California, Riverside [email protected] <http://web.chem.ucsb.edu/~neuman/orgchembyneuman/> Chapter Outline of the Book ************************************************************************************** I. Foundations 1. Organic Molecules and Chemical Bonding 2. Alkanes and Cycloalkanes 3. Haloalkanes, Alcohols, Ethers, and Amines 4. Stereochemistry 5. Organic Spectrometry II. Reactions, Mechanisms, Multiple Bonds 6. Organic Reactions *(Not yet Posted) 7. Reactions of Haloalkanes, Alcohols, and Amines. Nucleophilic Substitution 8. Alkenes and Alkynes 9. Formation of Alkenes and Alkynes. Elimination Reactions 10. Alkenes and Alkynes. Addition Reactions 11. Free Radical Addition and Substitution Reactions III. Conjugation, Electronic Effects, Carbonyl Groups 12. Conjugated and Aromatic Molecules 13. Carbonyl Compounds. Ketones, Aldehydes, and Carboxylic Acids 14. Substituent Effects 15. Carbonyl Compounds. Esters, Amides, and Related Molecules IV. Carbonyl and Pericyclic Reactions and Mechanisms 16. Carbonyl Compounds. Addition and Substitution Reactions 17. Oxidation and Reduction Reactions 18. Reactions of Enolate Ions and Enols 19. Cyclization and Pericyclic Reactions *(Not yet Posted) V. Bioorganic Compounds 20. Carbohydrates 21. Lipids 22. Peptides, Proteins, and α−Amino Acids 23. Nucleic Acids ************************************************************************************** -
Alternative Biochemistries for Alien Life: Basic Concepts and Requirements for the Design of a Robust Biocontainment System in Genetic Isolation
G C A T T A C G G C A T genes Review Alternative Biochemistries for Alien Life: Basic Concepts and Requirements for the Design of a Robust Biocontainment System in Genetic Isolation Christian Diwo 1 and Nediljko Budisa 1,2,* 1 Institut für Chemie, Technische Universität Berlin Müller-Breslau-Straße 10, 10623 Berlin, Germany; [email protected] 2 Department of Chemistry, University of Manitoba, 144 Dysart Rd, 360 Parker Building, Winnipeg, MB R3T 2N2, Canada * Correspondence: [email protected] or [email protected]; Tel.: +49-30-314-28821 or +1-204-474-9178 Received: 27 November 2018; Accepted: 21 December 2018; Published: 28 December 2018 Abstract: The universal genetic code, which is the foundation of cellular organization for almost all organisms, has fostered the exchange of genetic information from very different paths of evolution. The result of this communication network of potentially beneficial traits can be observed as modern biodiversity. Today, the genetic modification techniques of synthetic biology allow for the design of specialized organisms and their employment as tools, creating an artificial biodiversity based on the same universal genetic code. As there is no natural barrier towards the proliferation of genetic information which confers an advantage for a certain species, the naturally evolved genetic pool could be irreversibly altered if modified genetic information is exchanged. We argue that an alien genetic code which is incompatible with nature is likely to assure the inhibition of all mechanisms of genetic information transfer in an open environment. The two conceivable routes to synthetic life are either de novo cellular design or the successive alienation of a complex biological organism through laboratory evolution. -
Expanding the Genetic Code Lei Wang and Peter G
Reviews P. G. Schultz and L. Wang Protein Science Expanding the Genetic Code Lei Wang and Peter G. Schultz* Keywords: amino acids · genetic code · protein chemistry Angewandte Chemie 34 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim DOI: 10.1002/anie.200460627 Angew. Chem. Int. Ed. 2005, 44,34–66 Angewandte Protein Science Chemie Although chemists can synthesize virtually any small organic molecule, our From the Contents ability to rationally manipulate the structures of proteins is quite limited, despite their involvement in virtually every life process. For most proteins, 1. Introduction 35 modifications are largely restricted to substitutions among the common 20 2. Chemical Approaches 35 amino acids. Herein we describe recent advances that make it possible to add new building blocks to the genetic codes of both prokaryotic and 3. In Vitro Biosynthetic eukaryotic organisms. Over 30 novel amino acids have been genetically Approaches to Protein encoded in response to unique triplet and quadruplet codons including Mutagenesis 39 fluorescent, photoreactive, and redox-active amino acids, glycosylated 4. In Vivo Protein amino acids, and amino acids with keto, azido, acetylenic, and heavy-atom- Mutagenesis 43 containing side chains. By removing the limitations imposed by the existing 20 amino acid code, it should be possible to generate proteins and perhaps 5. An Expanded Code 46 entire organisms with new or enhanced properties. 6. Outlook 61 1. Introduction The genetic codes of all known organisms specify the same functional roles to amino acid residues in proteins. Selectivity 20 amino acid building blocks. These building blocks contain a depends on the number and reactivity (dependent on both limited number of functional groups including carboxylic steric and electronic factors) of a particular amino acid side acids and amides, a thiol and thiol ether, alcohols, basic chain. -
New Constrained Amino Acids and Peptide Nucleic Acid Building Blocks for the Construction of Bio-Polymers Alexandra Gresika
New constrained amino acids and peptide nucleic acid building blocks for the construction of bio-polymers Alexandra Gresika To cite this version: Alexandra Gresika. New constrained amino acids and peptide nucleic acid building blocks for the construction of bio-polymers. Other. Université Côte d’Azur, 2018. English. NNT : 2018AZUR4104. tel-02073232 HAL Id: tel-02073232 https://tel.archives-ouvertes.fr/tel-02073232 Submitted on 19 Mar 2019 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. THÈSE DE DOCTORAT Nouveaux synthons contraints de type - amino acides et PNA en vue de l´élaboration de bio-foldamères New constrained amino acids and peptide nucleic acid building blocks for the construction of biopolymers Alexandra Gresika Molécules Bioactives Présentée en vue de l’obtention Devant le jury, composé de : du grade de docteur en Chimie Muriel Amblard, Directrice de Recherche d’Université Côte d’Azur CNRS, IBMM UMR 5247, Université de Dirigée par : Nadia Patino Montpellier Karine Alvarez, Chargée de Recherche Soutenue le : 16.11.2018 CNRS, AFBM UMR 7257, Université Aix- Marseille Mohamed Mehiri, Maître de Conférences, ICN UMR 7272, Université Côte d’Azur Nadia Patino, Professeur des Universités, ICN UMR 7272, Université Côte d’Azur 1 New constrained amino acids and peptide nucleic acid building blocks for the construction of bio-polymers. -
1. Nucleotides A. Pentose Sugars – 5-Carbon Sugar 1) Deoxyribose – in DNA 2) Ribose – in RNA B. Phosphate Group C. Nitroge
1. Nucleotides a. Pentose sugars – 5-Carbon sugar 1) Deoxyribose – in DNA 2) Ribose – in RNA b. Phosphate group c. Nitrogenous bases 1) Purines a) Adenine b) Guanine 2) Pyrimidines a) Cytosine b) Thymine 2. Types of Nucleic Acids a. DNA 1) Locations 2) Functions b. RNA 1) Locations 2) Functions E. High Energy Biomolecules 1. Adenosine triphosphate a. Uses 1) Active transport 2) Movement 3) Biosynthesis reactions b. Regeneration 1) ADP + Pi + Energy → ATP 4. Classes of proteins a. Structural – ex. Collagen, keratin b. Transport – Hemoglobin, many β-globulins c. Contractile – Actin and Myosin of muscle tissue d. Regulatory - Hormones e. Immunologic - Antibodies f. Clotting – Thrombin and Fibrin g. Osmotic - Albumin h. Catalytic – Enzymes 1) Characteristics of enzymes • Proteins (most); ribonucleoproteins (few/ribozymes) • Act as organic catalysts • Lower the activation energy of reactions • Not changed by the reaction • Bind to their substrates o Lock-and-key model of enzyme activity o Induced-fit model • Highly specific • Named by adding -ase to substrate name; e.g., maltose/maltase • May require cofactors which may be: o Nonprotein metal ions such as copper, manganese, potassium, sodium o Small organic molecules known as coenzymes. The B vitamins like thiamine (B1) riboflavin (B2) and nicotinamide are precursors of coenzymes. • May require activation; e.g., pepsinogen pepsin in stomach chief cells 4. Factors Affecting Enzyme Action • pH o pepsin (stomach) @ pH = 2; trypsin (small int.) @ pH = 8 • Temperature o Denatured by high temp’s. • Enzyme inhibitors o Competitive inhibitors o Noncompetitive inhibitors • Effect of substrate concentration and reversible reactions and the Law of Mass D. -
Biosynthesis of Ribosylthymine in the Transfer RNA of Streptococcus
Proc. Nat. Acad. Sci. USA Vol. 72, No. 2, pp. 528-530, February 1975 Biosynthesis of Ribosylthymine in the Transfer RNA of Streptococcus faecalis: A Folate-Dependent Methylation Not Involving S-Adenosylmethionine (thymine/tRNA modification/formate/[methyl-'4Clmethionine/GlT'C-loop) ANN S. DELK AND JESSE C. RABINOWITZ Department of Biochemistry, University of California, Berkeley, Calif. 94720 Communicated by Bruce Ames, November 18, 1974 ABSTRACT Ribosylthymine is not present in tRNA of to produce thymidine 5'-monophosphate, which is sub- Streptococcus faecalis grown in the absence of folic acid, sequently used in DNA synthesis. Because of the folate although this methylated residue does occur in the tRNA of this organism when it is grown in the presence of folate. requirement for T formation in S. faecalis, it appeared possible We have found that, unlike other methylated residues in that methylation of RNA in this organism, particularly in RNA of S. faecalis and other organisms, the methyl moiety the biosynthesis of T, involves a folate derivative and not of ribosylthymine of the tRNA of folate-sufficient S. S-adenosylmethionine. faecalis is not derived from S-adenosylmethionine. Pre- liminary evidence suggests that a folate derivative serves MATERIALS AND METHODS as the methyl donor in this methylation. Unless stated otherwise, S. faecalis (ATCC 8043) and Esche- When grown in the presence of folic acid, Streptococcus richia coli (MRE 600) were grown for several generations in faecalis, like other prokaryotes, initiates protein synthesis -
Multi-Enzymatic Cascades in the Synthesis of Modified Nucleosides
biomolecules Article Multi-Enzymatic Cascades in the Synthesis of Modified Nucleosides: Comparison of the Thermophilic and Mesophilic Pathways Ilja V. Fateev , Maria A. Kostromina, Yuliya A. Abramchik, Barbara Z. Eletskaya , Olga O. Mikheeva, Dmitry D. Lukoshin, Evgeniy A. Zayats , Maria Ya. Berzina, Elena V. Dorofeeva, Alexander S. Paramonov , Alexey L. Kayushin, Irina D. Konstantinova * and Roman S. Esipov Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry RAS, Miklukho-Maklaya 16/10, 117997 GSP, B-437 Moscow, Russia; [email protected] (I.V.F.); [email protected] (M.A.K.); [email protected] (Y.A.A.); [email protected] (B.Z.E.); [email protected] (O.O.M.); [email protected] (D.D.L.); [email protected] (E.A.Z.); [email protected] (M.Y.B.); [email protected] (E.V.D.); [email protected] (A.S.P.); [email protected] (A.L.K.); [email protected] (R.S.E.) * Correspondence: [email protected]; Tel.: +7-905-791-1719 ! Abstract: A comparative study of the possibilities of using ribokinase phosphopentomutase ! nucleoside phosphorylase cascades in the synthesis of modified nucleosides was carried out. Citation: Fateev, I.V.; Kostromina, Recombinant phosphopentomutase from Thermus thermophilus HB27 was obtained for the first time: M.A.; Abramchik, Y.A.; Eletskaya, a strain producing a soluble form of the enzyme was created, and a method for its isolation and B.Z.; Mikheeva, O.O.; Lukoshin, D.D.; chromatographic purification was developed. It was shown that cascade syntheses of modified nu- Zayats, E.A.; Berzina, M.Y..; cleosides can be carried out both by the mesophilic and thermophilic routes from D-pentoses: ribose, Dorofeeva, E.V.; Paramonov, A.S.; 2-deoxyribose, arabinose, xylose, and 2-deoxy-2-fluoroarabinose. -
DNA Stands for Deoxyribose Nucleic Acid
DNA and Protein Synthesis DNA • DNA stands for deoxyribose nucleic acid. • This chemical substance is found in the nucleus of all cells in all living organisms • DNA controls all the chemical changes which take place in cells • The kind of cell which is formed, (muscle, blood, nerve etc) is controlled by DNA Ribose is a sugar, like glucose, but with only five carbon atoms in its molecule. Deoxyribose is almost the same but lacks one oxygen atom. The nitrogen bases are: o ADENINE (A) o THYMINE (T) o CYTOSINE (C) o GUANINE (G) Nucleotides • A molecule of DNA is formed by millions of nucleotides joined together in a long chain. • DNA is a very large molecule made up of a long chain of sub-units. • The sub-units are called nucleotides. • Each nucleotide is made up of a sugar called deoxyribose, a phosphate group -PO4 and an organic (Nitrogen) base: A, T, C, G BASE PAIRING RULE amount of C= amount of G AND amount of A= amount of T • Adenine always pairs with thymine, and guanine always pairs with cytosine. DNA STRUCTURE • The nucleotide bases will point to the inside of the DNA molecule while the outside (backbone) of the DNA molecule will be made of the sugar and phosphate molecules. • When complete the DNA molecule forms a double helix (two spiral sides wrapped together). • The paired strands are coiled into a spiral called A DOUBLE HELIX. Genes • Each chromosome contains hundreds of genes. • Most of your characteristics: hair color, height, how things taste to a person, are determined by the kinds of proteins cells make (gene). -
(12) United States Patent (10) Patent No.: US 8,604,000 B2 De Kort Et Al
USOO8604000B2 (12) United States Patent (10) Patent No.: US 8,604,000 B2 de Kort et al. (45) Date of Patent: Dec. 10, 2013 (54) PALATABLE NUTRITIONAL COMPOSITION 2011/0027391 A1 2/2011 De Kort et al. COMPRISING ANUCLEOTDE AND/ORA 2013, OO12469 A1 1/2013 De Kort et al. NUCLEOSDE AND A TASTE MASKING 2013, OO18012 A1 1/2013 Hageman et al. AGENT FOREIGN PATENT DOCUMENTS (75) Inventors: Esther Jacqueline de Kort, Wageningen EP O 175468 A2 3, 1986 (NL); Martine Groenendijk, EP 1216 041 B1 6, 2002 EP 1282 365 B1 2, 2003 Barendrecht (NL); Patrick Joseph EP 1656 839 A1 5, 2006 Gerardus Hendrikus Kamphuis, EP 1666 092 A2 6, 2006 Utrecht (NL) EP 18OO 675 A1 6, 2007 JP 64-080250 A 3, 1989 (73) Assignee: N.V. Nutricia, Zoetermeer (NL) JP 06-237734. A 8, 1994 JP 10-004918 A 1, 1998 JP 10-136937 A 5, 1998 (*) Notice: Subject to any disclaimer, the term of this JP 11-071274. A 3, 1999 patent is extended or adjusted under 35 WO WO-0038829 A1 T 2000 U.S.C. 154(b) by 213 days. WO WO-01 (32034 A1 5, 2001 WO WO-02/088159 A1 11, 2002 WO WO-02/096464 A1 12/2002 (21) Appl. No.: 12/809,431 WO WO-03 (013276 A1 2, 2003 WO WO-03/041701 A2 5, 2003 (22) PCT Filed: Dec. 22, 2008 WO WO-2005/039597 A2 5, 2005 WO WO-2006/031683 A2 3, 2006 (86). PCT No.: PCT/NL2O08/050843 WO WO-2006,118665 A2 11/2006 WO WO-2006, 127620 A2 11/2006 S371 (c)(1), WO WO-2007/001883 A2 1, 2007 (2), (4) Date: Dec.