FfAME:org :: Hyo-Joong Kim's Publications

Setting the Stage: The History, Chemistry, and Geobiology behind RNA
Benner, SA; Kim, HJ; Yang, ZY
RNA Worlds: From Life's Origins to Diversity in Gene Regulation , ed. John F. Atkins, Raymond F. Gesteland, Thomas R. Cech , Cold Spring Harbor Laboratory Press 7-19 (2011)

2'-Deoxy-1-methylpseudocytidine, a stable analog of 2'-deoxy-5-methylisocytidine
Kim, HJ; Leal, NA; Benner, SA
Bioorg. Med. Chem. 17 (10) 3728-3732 (2009)
<Abstract>

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. (C) 2009 Elsevier Ltd. All rights reserved.

Synthesis of pyrophosphates for in vitro selection of catalytic RNA molecules
Kim, HJ; Kim, MJ; Karalkar, N; Hutter, D; Benner, SA
Nuc. Nuc. Nuc. acids 27 43-56 (2008)

Synthesis and antiviral activity of 7-deazaneplanocin A against orthopoxviruses (vaccinia and cowpox virus)
Arumugham, B; Kim, HJ; Prichard, MN; Kern, ER; Chu, CK
Bioorg. Med. Chem. Lett. 16 (2) 285-287 (2006)
<Abstract>

An efficient method for the synthesis of 7-deazaneplanocin A (2) has been accomplished by the condensation of cyclopentenol 3 with 6-chloro-7-deazapurine followed by subsequent functional group manipulations. The synthesized 7-deazaneplanocin A (2) exhibited potent antiviral activity against cowpox and vaccinia viruses without cytotoxicity in HFF cells. (c) 2005 Elsevier Ltd. All rights reserved.

Reaction of tetramethylimidazol-2-ylidene with (Tp(tBu,Me))YbE(thf) (E=I, CH2SMe3): simple adduct and a hydrocarbyl tethered carbene ligand
Ferrence, GM; Arduengo, AJ; Jockisch, A; Kim, HJ; McDonald, R; Takats, J
J. Alloys Compd. 418 184-188 (2006)
<Abstract>

Treatment of (Tp(tBu,Me))YbE(thf) (E=I (1), CH2SiMe3 (2)) with tetramethylimidazol-2-ylidene (ImMe(4)) resulted in very different outcomes depending on the nature of the anionic ligand E. ImMe(4) acts as a simple Lewis base toward 1 resulting in substitution of the thf (tetrahydrofuran) ligand and formation of (Tp(tBu,Me))YbI(ImMe(4)) (3). However, reaction with 2, in addition to displacement of thf, proceeded by metalation of one of the N-CH3 substituents of ImMe(4) and gave (Tp(tBu,Me))Yb(ImMe(4))(CH2N(C(CH3)C(CH3)N(CH3)C) (4), featuring a hydrocarbyl tethered carbene ligand. The X-ray structures of 3 and 4 are reported. (c) 2006 Published by Elsevier B.V.

A stable dirhodium tetracarboxylate carbenoid: Crystal structure, bonding analysis, and catalysis
Snyder, JP; Padwa, A; Stengel, T; Arduengo, AJ; Jockisch, A; Kim, HJ
J. Am. Chem. Soc. 123 (45) 11318-11319 (2001)

Orthocyclophanes .3. Ketonands, Novel ketonic crowns of polyoxo[1(N)]orthocyclophane constitution
Lee, WY; Park, CH; Kim, HJ; Kim, SS
J. Org. Chem. 59 (4) 878-884 (1994)
<Abstract>

Synthetic studies of a new family of novel ketonic macrocycles are reported. Exhaustive oxidation of all of the methylenes in odd-numbered [1(n)]orthocyclophanes ([1(n)]OCPs) resulted in the polyoxo derivatives of a cyclopolyorthobenzoyl or polyoxo[1(n)]orthocyclophane constitution. This new class of ketonic crowns is referred to as [1(n)]orthocyclophanepolyones and includes [1(5)] orthocyclophane-pentaone, [1(7)]orthocyclophaneheptaone, and [1(9)]orthocyclophanenonaone. We suggest the generic name ''ketonands'' for these ketonic crowns. Structures of ketonands were confirmed by spectral and X-ray crystallographic analyses.

Biscyclophanes .2. Regioselectivity in the acid-catalyzed cycloalkylation of benzylbenzylic alcohol (BBA)
Lee, WY; Sim, WB; Kim, HJ; Yoon, SH
J. Chem. Soc., Perkin Trans. 1 (6) 719-729 (1993)
<Abstract>

o-Benzylbenzylic alcohols (o-BBAs), in which the terminal benzyl alcohol is substituted by repeating benzyl chains all in the ortho sense, have been found to have conspicuous regioselectivity in acid-catalysed cycloalkylation, giving rise to various cyclophanes as intramolecular Friedel-Crafts alkylation products. The structure of the cyclisation products was largely dependent upon the size of the benzylic alcohols. Acidic treatment of 2-nuclear o-BBA 6 gave a [1.1]orthocyclophane 7 with a 6-membered ring, whereas 3-nuclear o-BBA 1 afforded [1.1.1]orthocyclophane 2 with a 9-membered ring in preference to a 6-membered-ring product. Higher homologues, such as 4- and 5-nuclear o-BBAs, gave rise to [1.(4)](1,2)(1,2)(1,2)(1,3)cyclophanes 14 and 25 with a 13-membered ring unit, respectively. Cyclophanes with a larger-than-1 3-membered ring have never been isolated as cycloalkylation products of o- BBA. Generalisations have been made about the priority of formation of cycles in the cycloalkylation of o-BBA in acid, to give a cycloalkylation rule, which involves the priority order of 13-membered ring > 9-membered ring > 6-membered ring. The regioselectivity was consistent with the acid-catalysed cycloalkylation of alpha,omega-benzylbenzylic diols, which yielded common-nuclear biscyclophanes. The sizes and structures of the biscyclophane products are also dependent upon the sizes and structures of the terminal benzylic diols.