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Dive into the research topics where Hyo-Joong Kim is active.

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Featured researches published by Hyo-Joong Kim.


Journal of the American Chemical Society | 2015

Evolution of Functional Six-Nucleotide DNA

Liqin Zhang; Zunyi Yang; Kwame Sefah; Kevin M. Bradley; Shuichi Hoshika; Myong-Jung Kim; Hyo-Joong Kim; Guizhi Zhu; Elizabeth Jiménez; Sena Cansiz; I-Ting Teng; Carole Champanhac; Christopher McLendon; Chen Liu; Wen Zhang; Dietlind L. Gerloff; Zhen Huang; Weihong Tan; Steven A. Benner

Axiomatically, the density of information stored in DNA, with just four nucleotides (GACT), is higher than in a binary code, but less than it might be if synthetic biologists succeed in adding independently replicating nucleotides to genetic systems. Such addition could also add functional groups not found in natural DNA, but useful for molecular performance. Here, we consider two new nucleotides (Z and P, 6-amino-5-nitro-3-(1-β-D-2-deoxyribo-furanosyl)-2(1H)-pyridone and 2-amino-8-(1-β-D-2-deoxyribofuranosyl)-imidazo[1,2-a]-1,3,5-triazin-4(8H)-one). These are designed to pair via complete Watson-Crick geometry. These were added to a library of oligonucleotides used in a laboratory in vitro evolution (LIVE) experiment; the GACTZP library was challenged to deliver molecules that bind selectively to liver cancer cells, but not to untransformed liver cells. Unlike in classical in vitro selection, low levels of mutation allow this system to evolve to create binding molecules not necessarily present in the original library. Over a dozen binding species were recovered. The best had Z and/or P in their sequences. Several had multiple, nearby, and adjacent Zs and Ps. Only the weaker binders contained no Z or P at all. This suggests that this system explored much of the sequence space available to this genetic system and that GACTZP libraries are richer reservoirs of functionality than standard libraries.


Astrobiology | 2013

The “Strong” RNA World Hypothesis: Fifty Years Old

Marc Neveu; Hyo-Joong Kim; Steven A. Benner

This year marks the 50(th) anniversary of a proposal by Alex Rich that RNA, as a single biopolymer acting in two capacities, might have supported both genetics and catalysis at the origin of life. We review here both published and previously unreported experimental data that provide new perspectives on this old proposal. The new data include evidence that, in the presence of borate, small amounts of carbohydrates can fix large amounts of formaldehyde that are expected in an environment rich in carbon dioxide. Further, we consider other species, including arsenate, arsenite, phosphite, and germanate, that might replace phosphate as linkers in genetic biopolymers. While linkages involving these oxyanions are judged to be too unstable to support genetics on Earth, we consider the possibility that they might do so in colder semi-aqueous environments more exotic than those found on Earth, where cosolvents such as ammonia might prevent freezing at temperatures well below 273 K. These include the ammonia-water environments that are possibly present at low temperatures beneath the surface of Titan, Saturns largest moon.


Cold Spring Harbor Perspectives in Biology | 2012

Setting the Stage: The History, Chemistry, and Geobiology behind RNA

Steven A. Benner; Hyo-Joong Kim; Zunyi Yang

No community-accepted scientific methods are available today to guide studies on what role RNA played in the origin and early evolution of life on Earth. Further, a definition-theory for life is needed to develop hypotheses relating to the RNA First model for the origin of life. Four approaches are currently at various stages of development of such a definition-theory to guide these studies. These are (a) paleogenetics, in which inferences about the structure of past life are drawn from the structure of present life; (b) prebiotic chemistry, in which hypotheses with experimental support are sought that get RNA from organic and inorganic species possibly present on early Earth; (c) exploration, hoping to encounter life independent of terran life, which might contain RNA; and (d) synthetic biology, in which laboratories attempt to reproduce biological behavior with unnatural chemical systems.


Cold Spring Harbor Perspectives in Biology | 2010

Planetary Organic Chemistry and the Origins of Biomolecules

Steven A. Benner; Hyo-Joong Kim; Myung-Jung Kim; Alonso Ricardo

Organic chemistry on a planetary scale is likely to have transformed carbon dioxide and reduced carbon species delivered to an accreting Earth. According to various models for the origin of life on Earth, biological molecules that jump-started Darwinian evolution arose via this planetary chemistry. The grandest of these models assumes that ribonucleic acid (RNA) arose prebiotically, together with components for compartments that held it and a primitive metabolism that nourished it. Unfortunately, it has been challenging to identify possible prebiotic chemistry that might have created RNA. Organic molecules, given energy, have a well-known propensity to form multiple products, sometimes referred to collectively as tar or tholin. These mixtures appear to be unsuited to support Darwinian processes, and certainly have never been observed to spontaneously yield a homochiral genetic polymer. To date, proposed solutions to this challenge either involve too much direct human intervention to satisfy many in the community, or generate molecules that are unreactive dead ends under standard conditions of temperature and pressure. Carbohydrates, organic species having carbon, hydrogen, and oxygen atoms in a ratio of 1:2:1 and an aldehyde or ketone group, conspicuously embody this challenge. They are components of RNA and their reactivity can support both interesting spontaneous chemistry as part of a carbohydrate world, but they also easily form mixtures, polymers and tars. We describe here the latest thoughts on how on this challenge, focusing on how it might be resolved using minerals containing borate, silicate, and molybdate, inter alia.


Science | 2010

Comment on “The Silicate-Mediated Formose Reaction: Bottom-Up Synthesis of Sugar Silicates”

Hyo-Joong Kim; Steven A. Benner

Lambert et al. (Reports, 19 February 2010, p. 984) reported that silicate ions catalyze the formation and stabilization of four- and six-carbon sugars from simple sugars, suggesting a possible prebiotic pathway for the synthesis of biologically important sugars. Here, we show that silicate has minimal impact in these respects, especially when compared to borate minerals.


Angewandte Chemie | 2016

Evaporite Borate‐Containing Mineral Ensembles Make Phosphate Available and Regiospecifically Phosphorylate Ribonucleosides: Borate as a Multifaceted Problem Solver in Prebiotic Chemistry

Hyo-Joong Kim; Yoshihiro Furukawa; Takeshi Kakegawa; Andrei Bita; Romulus Ion Scorei; Steven A. Benner

RNA is currently thought to have been the first biopolymer to support Darwinian natural selection on Earth. However, the phosphate esters in RNA and its precursors, and the many sites at which phosphorylation might occur in ribonucleosides under conditions that make it possible, challenge prebiotic chemists. Moreover, free inorganic phosphate may have been scarce on early Earth owing to its sequestration by calcium in the unreactive mineral hydroxyapatite. Herein, it is shown that these problems can be mitigated by a particular geological environment that contains borate, magnesium, sulfate, calcium, and phosphate in evaporite deposits. Actual geological environments, reproduced here, show that Mg2+ and borate sequester phosphate from calcium to form the mineral lüneburgite. Ribonucleosides stabilized by borate mobilize borate and phosphate from lüneburgite, and are then regiospecifically phosphorylated by the mineral. Thus, in addition to guiding carbohydrate pre-metabolism, borate minerals in evaporite geoorganic contexts offer a solution to the phosphate problem in the RNA first model for the origins of life.


Journal of Organic Chemistry | 2012

Synthesis and properties of 5-cyano-substituted nucleoside analog with a donor-donor-acceptor hydrogen-bonding pattern.

Hyo-Joong Kim; Fei Chen; Steven A. Benner

6-Aminopyridin-2-ones form Watson-Crick pairs with complementary purine analogues to add a third nucleobase pair to DNA and RNA, if an electron-withdrawing group at position 5 slows oxidation and epimerization. In previous work with a nucleoside analogue trivially named dZ, the electron withdrawing unit was a nitro group. Here, we describe an analogue of dZ (cyano-dZ) having a cyano group instead of a nitro group, including its synthesis, pK(a), rates of acid-catalyzed epimerization, and enzymatic incorporation.


Bioorganic & Medicinal Chemistry | 2009

2'-deoxy-1-methylpseudocytidine, a stable analog of 2'-deoxy-5-methylisocytidine.

Hyo-Joong Kim; Nicole A. Leal; Steven A. Benner

2-deoxy-5-methylisocytidine is widely used in assays to personalize the care of patients infected with HIV, hepatitis C, and other infectious agents. However, oligonucleotides that incorporate 2-deoxy-5-methylisocytidine are expensive, because of its intrinsic chemical instability. We report here a C-glycoside analog that is more stable and, in oligonucleotides, pairs with 2-deoxyisoguanosine, contributing to duplex stability about as much as a standard 2-deoxycytidine and 2-deoxyguanosine pair.


Angewandte Chemie | 2015

A Crystal Structure of a Functional RNA Molecule Containing an Artificial Nucleobase Pair.

Armando R. Hernandez; Yaming Shao; Shuichi Hoshika; Zunyi Yang; Sandip A. Shelke; Julien Herrou; Hyo-Joong Kim; Myong-Jung Kim; Joseph A. Piccirilli; Steven A. Benner

As one of its goals, synthetic biology seeks to increase the number of building blocks in nucleic acids. While efforts towards this goal are well advanced for DNA, they have hardly begun for RNA. Herein, we present a crystal structure for an RNA riboswitch where a stem C:G pair has been replaced by a pair between two components of an artificially expanded genetic-information system (AEGIS), Z and P, (6-amino-5-nitro-2(1H)-pyridone and 2-amino-imidazo[1,2-a]-1,3,5-triazin-4-(8H)-one). The structure shows that the Z:P pair does not greatly change the conformation of the RNA molecule nor the details of its interaction with a hypoxanthine ligand. This was confirmed in solution by in-line probing, which also measured a 3.7u2005nM affinity of the riboswitch for guanine. These data show that the Z:P pair mimics the natural Watson-Crick geometry in RNA in the first example of a crystal structure of an RNA molecule that contains an orthogonal added nucleobase pair.


Nucleosides, Nucleotides & Nucleic Acids | 2008

Synthesis of Pyrophosphates for In Vitro Selection of Catalytic RNA Molecules

Hyo-Joong Kim; Myong Kim; Nilesh Karalkar; Daniel Hutter; Steven A. Benner

Reported here are synthetic routes to pyrophosphates linking riboflavin with various nucleosides. The focus is on a flavin-uracil dinucleotide having a biotin tag on the uracil, a molecule that has potential value in the selection of RNA enzymes that catalyze the template-directed polymerization of RNA in the 3′-to-5′ direction, which is the direction opposite that catalyzed by standard protein polymerases. Two detailed procedures are presented to prepare this new compound, as well as one procedure to prepare the new flavin-2,6-diaminopurine dinucleotide.

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Zunyi Yang

University of Southern California

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Myong Kim

Seoul National University

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Woo-Young Lee

Seoul National University

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