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Nucleosides, Nucleotides & Nucleic Acids Volume 20, 2001 - Issue 9
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Original Articles

SYNTHESIS OF SELENIUM-DERIVATIZED NUCLEOSIDES AND OLIGONUCLEOTIDES FOR X-RAY CRYSTALLOGRAPHY

Nicolas Carrasco Department of Chemistry, Brooklyn College, and Program of Biochemistry and Chemistry, The Graduate School of The City University of New York, 2900 Bedford Ave., Brooklyn, New York, 11210, U.S.A.
,
Dov Ginsburg Department of Chemistry, Brooklyn College, and Program of Biochemistry and Chemistry, The Graduate School of The City University of New York, 2900 Bedford Ave., Brooklyn, New York, 11210, U.S.A.
,
Quan Du Department of Chemistry, Brooklyn College, and Program of Biochemistry and Chemistry, The Graduate School of The City University of New York, 2900 Bedford Ave., Brooklyn, New York, 11210, U.S.A.
&
Zhen Huang Department of Chemistry, Brooklyn College, and Program of Biochemistry and Chemistry, The Graduate School of The City University of New York, 2900 Bedford Ave., Brooklyn, New York, 11210, U.S.A.
Pages 1723-1734 | Received 30 Dec 2000, Accepted 06 Apr 2001, Published online: 21 Aug 2006

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Chong Zhang, Shanshan Qin, Bei Hu, Jiazhen Lv, Zhaoyi Yang, Weizhu Yan, Jun Wang, Niu Huang & Zhen Huang. (2019) Disruption of nucleobase stacking to restore reactivity. Nucleosides, Nucleotides & Nucleic Acids 38:8, pages 567-577.
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Jozef Salon, Bo Zhang & Zhen Huang. (2011) Mild Detritylation of Nucleic Acid Hydroxyl Groups by Warming Up. Nucleosides, Nucleotides & Nucleic Acids 30:4, pages 271-279.
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Lina Lin, Jia Sheng, RazinK. Momin, Quan Du & Zhen Huang. (2009) Facile Synthesis and Anti-Tumor Cell Activity of Se-Containing Nucleosides. Nucleosides, Nucleotides & Nucleic Acids 28:1, pages 56-66.
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Articles from other publishers (58)

Ziyuan Fang, Yuliya Dantsu, Cen Chen, Wen Zhang & Zhen Huang. (2023) Synthesis of Pyrimidine Modified Seleno‐DNA as a Novel Approach to Antisense Candidate. ChemistrySelect 8:25.
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Cen Chen, Fukang Yang & Zhen Huang. 2023. Nucleic Acids in Medicinal Chemistry and Chemical Biology. Nucleic Acids in Medicinal Chemistry and Chemical Biology 113 131 .
Cen Chen, Ziyuan Fang & Zhen Huang. (2022) 2′-β-Selenium Atom on Thymidine to Control β-Form DNA Conformation and Large Crystal Formation. Crystal Growth & Design 22:6, pages 3601-3604.
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Peipei Jin, Xueli Wang, Haifeng Pan & Jinquan Chen. (2022) One order of magnitude increase of triplet state lifetime observed in deprotonated form selenium substituted uracil. Physical Chemistry Chemical Physics 24:2, pages 875-882.
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Patrick F. Conlon, Olga Eguaogie, Jordan J. Wilson, Jamie S. T. Sweet, Julian Steinhoegl, Klaudia Englert, Oliver G. A. Hancox, Christopher J. Law, Sarah A. Allman, James H. R. Tucker, James P. Hall & Joseph S. Vyle. (2019) Solid-phase synthesis and structural characterisation of phosphoroselenolate-modified DNA: a backbone analogue which does not impose conformational bias and facilitates SAD X-ray crystallography. Chemical Science 10:47, pages 10948-10957.
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Christopher Liczner, Vincent Grenier & Christopher J. Wilds. (2018) Reversible diselenide cross-links are formed between oligonucleotides containing 2′-deoxy-6-selenoinosine. Tetrahedron Letters 59:1, pages 38-41.
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Marta Sosnowska, Samanta Makurat, Magdalena Zdrowowicz & Janusz Rak. (2017) 5-Selenocyanatouracil: A Potential Hypoxic Radiosensitizer. Electron Attachment Induced Formation of Selenium Centered Radical. The Journal of Physical Chemistry B 121:25, pages 6139-6147.
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Qiulong Zhang, Huanhuan Lv, Lili Wang, Man Chen, Fangfei Li, Chao Liang, Yuanyuan Yu, Feng Jiang, Aiping Lu & Ge Zhang. (2016) Recent Methods for Purification and Structure Determination of Oligonucleotides. International Journal of Molecular Sciences 17:12, pages 2134.
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Wen Zhang, Jack W. Szostak & Zhen Huang. (2016) Nucleic acid crystallization and X-ray crystallography facilitated by single selenium atom. Frontiers of Chemical Science and Engineering 10:2, pages 196-202.
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Huiyan Sun, Sibo Jiang & Zhen Huang. 2016. Nucleic Acid Crystallography. Nucleic Acid Crystallography 193 204 .
N. Tarashima, T. Sumitomo, H. Ando, K. Furukawa, T. Ishida & N. Minakawa. (2015) Synthesis of DNA fragments containing 2′-deoxy-4′-selenonucleoside units using DNA polymerases: comparison of dNTPs with O, S and Se at the 4′-position in replication. Organic & Biomolecular Chemistry 13:25, pages 6949-6952.
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Rob Abdur & Zhen Huang. 2016. Atypical Elements in Drug Design. Atypical Elements in Drug Design 119 153 .
Zvi RappoportAnna Maciaszek, Agnieszka Tomaszewska & Piotr Guga. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups 1 42 .
Rob Abdur, Oksana O. Gerlits, Jianhua Gan, Jiansheng Jiang, Jozef Salon, Andrey Y. Kovalevsky, Alexander A. Chumanevich, Irene T. Weber & Zhen Huang. (2014) Novel complex MAD phasing and RNase H structural insights using selenium oligonucleotides. Acta Crystallographica Section D Biological Crystallography 70:2, pages 354-361.
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Manindar Kaur & Zhen Huang. (2013) Synthesis and optical behaviors of 6-seleno-deoxyguanosine. Science China Chemistry 57:2, pages 314-321.
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Jia Sheng, Jianhua Gan, Alexei S. Soares, Jozef Salon & Zhen Huang. (2013) Structural insights of non-canonical U•U pair and Hoogsteen interaction probed with Se atom. Nucleic Acids Research 41:22, pages 10476-10487.
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Huiyan Sun, Sibo Jiang, Julianne Caton-Williams, Hehua Liu & Zhen Huang. (2013) 2-Selenouridine triphosphate synthesis and Se-RNA transcription. RNA 19:9, pages 1309-1314.
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Jia Sheng, Jianhua Gan & Zhen Huang. (2013) Structure-Based DNA-Targeting Strategies with Small Molecule Ligands for Drug Discovery. Medicinal Research Reviews 33:5, pages 1119-1173.
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Jozef Salon, Jianhua Gan, Rob Abdur, Hehua Liu & Zhen Huang. (2013) Synthesis of 6-Se-Guanosine RNAs for Structural Study. Organic Letters 15:15, pages 3934-3937.
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Peixuan Guo & Farzin HaqueHuiyan Sun & Zhen Huang. 2013. RNA Nanotechnology and Therapeutics. RNA Nanotechnology and Therapeutics 213 234 .
Wen Zhang, E. Abdalla Hassan & Zhen Huang. (2012) Synthesis of novel di-Se-containing thymidine and Se-DNAs for structure and function studies. Science China Chemistry 56:3, pages 273-278.
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Julianne Caton‐Williams, Rudiona Hoxhaj, Bilal Fiaz & Zhen Huang. (2013) Use of a Novel 5′‐Regioselective Phosphitylating Reagent for One‐Pot Synthesis of Nucleoside 5′‐Triphosphates from Unprotected Nucleosides. Current Protocols in Nucleic Acid Chemistry 52:1.
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Manindar Kaur, Abdur Rob, Julianne Caton-Williams & Zhen Huang. 2013. Biochalcogen Chemistry: The Biological Chemistry of Sulfur, Selenium, and Tellurium. Biochalcogen Chemistry: The Biological Chemistry of Sulfur, Selenium, and Tellurium 89 126 .
Sibo Jiang, Huiyan Sun & Zhen Huang. 2013. DNA Nanotechnology. DNA Nanotechnology 29 56 .
Sibo Jiang, Jia Sheng & Zhen Huang. (2011) Synthesis of the Tellurium‐Derivatized Phosphoramidites and Their Incorporation into DNA Oligonucleotides. Current Protocols in Nucleic Acid Chemistry 47:1.
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Lina Lin, Julianne Caton-Williams, Manindar Kaur, Andres M. Patino, Jia Sheng, Jaya Punetha & Zhen Huang. (2011) Facile synthesis of nucleoside 5′-(α-P-seleno)-triphosphates and phosphoroselenoate RNA transcription. RNA 17:10, pages 1932-1938.
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Wen Zhang, Jia Sheng & Zhen Huang. 2011. Medicinal Chemistry of Nucleic Acids. Medicinal Chemistry of Nucleic Acids 101 141 .
Vanessa Siegmund, Tobias Santner, Ronald Micura & Andreas Marx. (2011) Enzymatic synthesis of 2′-methylseleno-modified RNA. Chemical Science 2:11, pages 2224.
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Lina Lin, Jia Sheng & Zhen Huang. (2011) Nucleic acid X-ray crystallography via direct selenium derivatization. Chemical Society Reviews 40:9, pages 4591.
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Jia Sheng & Zhen Huang. (2010) Selenium Derivatization of Nucleic Acids for X‐Ray Crystal‐Structure and Function Studies. Chemistry & Biodiversity 7:4, pages 753-785.
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Jozef Salon, Jia Sheng, Jianhua Gan & Zhen Huang. (2010) Synthesis and Crystal Structure of 2′-Se-Modified Guanosine Containing DNA. The Journal of Organic Chemistry 75:3, pages 637-641.
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Jia Sheng, Jozef Salon, JianHua Gan & Zhen Huang. (2010) Synthesis and crystal structure study of 2′-Se-adenosine-derivatized DNA. Science China Chemistry 53:1, pages 78-85.
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Jia Sheng, Abdalla E. A. Hassan & Zhen Huang. (2009) Synthesis of the First Tellurium-Derivatized Oligonucleotides for Structural and Functional Studies. Chemistry - A European Journal 15:39, pages 10210-10216.
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Abdalla E. A. Hassan, Jia Sheng, Jiansheng Jiang, Wen Zhang & Zhen Huang. (2009) Synthesis and Crystallographic Analysis of 5-Se-Thymidine DNAs. Organic Letters 11:12, pages 2503-2506.
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K. C. Kumara Swamy, N. N. Bhuvan Kumar, E. Balaraman & K. V. P. Pavan Kumar. (2009) Mitsunobu and Related Reactions: Advances and Applications. Chemical Reviews 109:6, pages 2551-2651.
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Jozef Salon, Jiansheng Jiang, Jia Sheng, Oksana O. Gerlits & Zhen Huang. (2008) Derivatization of DNAs with selenium at 6-position of guanine for function and crystal structure studies. Nucleic Acids Research 36:22, pages 7009-7018.
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Jonathan K. Watts, Blair D. Johnston, Kumarasamy Jayakanthan, Alexander S. Wahba, B. Mario Pinto & Masad J. Damha. (2008) Synthesis and Biophysical Characterization of Oligonucleotides Containing a 4′-Selenonucleotide. Journal of the American Chemical Society 130:27, pages 8578-8579.
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Jia Sheng, Abdalla E. A. Hassan & Zhen Huang. (2008) New Telluride-Mediated Elimination for Novel Synthesis of 2′,3′-Didehydro-2′,3′-dideoxynucleosides. The Journal of Organic Chemistry 73:10, pages 3725-3729.
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Jia Sheng & Zhen Huang. (2008) Selenium Derivatization of Nucleic Acids for Phase and Structure Determination in Nucleic Acid X-ray Crystallography. International Journal of Molecular Sciences 9:3, pages 258-271.
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Julianne Caton‐Williams & Zhen Huang. (2008) Biochemistry of Selenium‐Derivatized Naturally Occurring and Unnatural Nucleic Acids. Chemistry & Biodiversity 5:3, pages 396-407.
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Jia Sheng & Zhen Huang. (2008) Synthesis of a 4‐Selenothymidine Phosphoramidite and Incorporation into Oligonucleotides. Current Protocols in Nucleic Acid Chemistry 32:1.
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Julianne Caton‐Williams & Zhen Huang. (2008) Synthesis and DNA‐Polymerase Incorporation of Colored 4‐Selenothymidine Triphosphate for Polymerase Recognition and DNA Visualization. Angewandte Chemie International Edition 47:9, pages 1723-1725.
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Julianne Caton-Williams & Zhen Huang. (2008) Synthesis and DNA-Polymerase Incorporation of Colored 4-Selenothymidine Triphosphate for Polymerase Recognition and DNA Visualization. Angewandte Chemie 120:9, pages 1747-1749.
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Kha Tram, Xiaolu Wang & Hongbin Yan. (2007) Facile Synthesis of Oligonucleotide Phosphoroselenoates. Organic Letters 9:24, pages 5103-5106.
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Jozef Salon, Jia Sheng, Jiansheng Jiang, Guexiong Chen, Julianne Caton-Williams & Zhen Huang. (2007) Oxygen Replacement with Selenium at the Thymidine 4-Position for the Se Base Pairing and Crystal Structure Studies. Journal of the American Chemical Society 129:16, pages 4862-4863.
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Jia Sheng, Jiansheng Jiang, Jozef Salon & Zhen Huang. (2007) Synthesis of a 2‘-Se-thymidine Phosphoramidite and Its Incorporation into Oligonucleotides for Crystal Structure Study. Organic Letters 9:5, pages 749-752.
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Adam P. Silverman & Eric T. Kool. 2007. 79 115 .
Barbara L. Golden. 2007. Macromolecular Crystallography Protocols. Macromolecular Crystallography Protocols 239 257 .
Nicolas Carrasco, Julianne Caton‐Williams, Gary Brandt, Siming Wang & Zhen Huang. (2005) Efficient Enzymatic Synthesis of Phosphoroselenoate RNA by Using Adenosine 5′‐(α‐ P ‐Seleno)triphosphate . Angewandte Chemie International Edition 45:1, pages 94-97.
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Nicolas Carrasco, Julianne Caton‐Williams, Gary Brandt, Siming Wang & Zhen Huang. (2005) Efficient Enzymatic Synthesis of Phosphoroselenoate RNA by Using Adenosine 5′‐(α‐ P ‐Seleno)triphosphate . Angewandte Chemie 118:1, pages 100-103.
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Jozef Salon, Guexiong Chen, Yoani Portilla, Markus W. Germann & Zhen Huang. (2005) Synthesis of a 2‘-Se-uridine Phosphoramidite and Its Incorporation into Oligonucleotides for Structural Study. Organic Letters 7:25, pages 5645-5648.
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Piotr Guga, Anna Maciaszek & Wojciech J. Stec. (2005) Oxathiaphospholane Approach to the Synthesis of Oligodeoxyribonucleotides Containing Stereodefined Internucleotide Phosphoroselenoate Function † . Organic Letters 7:18, pages 3901-3904.
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Yuri Buzin, Nicolas Carrasco & Zhen Huang. (2004) Synthesis of Selenium-Derivatized Cytidine and Oligonucleotides for X-ray Crystallography Using MAD. Organic Letters 6:7, pages 1099-1102.
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Claudia Höbartner & Ronald Micura. (2004) Chemical Synthesis of Selenium-Modified Oligoribonucleotides and Their Enzymatic Ligation Leading to an U6 SnRNA Stem−Loop Segment. Journal of the American Chemical Society 126:4, pages 1141-1149.
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Nicolas Carrasco & Zhen Huang. (2003) Enzymatic Synthesis of Phosphoroselenoate DNA Using Thymidine 5‘-(α-P- seleno)triphosphate and DNA Polymerase for X-ray Crystallography via MAD. Journal of the American Chemical Society 126:2, pages 448-449.
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Marianna Teplova, Christopher J. Wilds, Zdzislaw Wawrzak, Valentina Tereshko, Quan Du, Nicolas Carrasco, Zhen Huang & Martin Egli. (2002) Covalent incorporation of selenium into oligonucleotides for X-ray crystal structure determination via MAD: proof of principle. Biochimie 84:9, pages 849-858.
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Nicolas Carrasco, Dov Ginsburg, Quan Du & Zhen Huang. (2010) ChemInform Abstract: Synthesis of Selenium‐Derivatized Nucleosides and Oligonucleotides for X‐Ray Crystallography.. ChemInform 33:8.
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Quan Du, Nicolas Carrasco, Marianna Teplova, Christopher J. Wilds, Martin Egli & Zhen Huang. (2001) Internal Derivatization of Oligonucleotides with Selenium for X-ray Crystallography Using MAD. Journal of the American Chemical Society 124:1, pages 24-25.
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