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Bioscience, Biotechnology, and Biochemistry Volume 76, 2012 - Issue 6
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Original Articles

Concise Synthesis of the Anti-HIV Nucleoside EFdA

Masayuki KAGEYAMALaboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
,
Takuho MIYAGILaboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
,
Mayumi YOSHIDALaboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
,
Tomohiro NAGASAWALaboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
,
Hiroshi OHRUIYokohama College of Pharmacy
&
Shigefumi KUWAHARALaboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
Pages 1219-1225 | Received 24 Feb 2012, Accepted 07 Mar 2012, Published online: 22 May 2014

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Mai Kamata, Toshifumi Takeuchi, Ei Hayashi, Kazane Nishioka, Mizuki Oshima, Masashi Iwamoto, Kota Nishiuchi, Shogo Kamo, Shusuke Tomoshige, Koichi Watashi, Shinji Kamisuki, Hiroshi Ohrui, Fumio Sugawara & Kouji Kuramochi. (2020) Synthesis of nucleotide analogues, EFdA, EdA and EdAP, and the effect of EdAP on hepatitis B virus replication. Bioscience, Biotechnology, and Biochemistry 84:2, pages 217-227.
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Articles from other publishers (13)

Cohan Huxley, Callum Lucas, Juan Manuel Mesa Bruno, Matthew J. Anketell, Emma K. Davison, Garrett Muir, Matthew B. Nodwell, Michael Meanwell, Steven M. Silverman, Robert Britton & Louis-Charles Campeau. (2023) Efficient protocol for the preparation of α-heteroaryl acetaldehydes. Canadian Journal of Chemistry.
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Regine Siedentop & Katrin Rosenthal. (2022) Industrially Relevant Enzyme Cascades for Drug Synthesis and Their Ecological Assessment. International Journal of Molecular Sciences 23:7, pages 3605.
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Stefan Simić, Erna Zukić, Luca Schmermund, Kurt Faber, Christoph K. Winkler & Wolfgang Kroutil. (2021) Shortening Synthetic Routes to Small Molecule Active Pharmaceutical Ingredients Employing Biocatalytic Methods. Chemical Reviews 122:1, pages 1052-1126.
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Phillip Clayman, Gheorghe-Doru Roiban & Douglas Fuerst. 2022. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering.
Jovana Nazor, Joyce Liu & Gjalt Huisman. (2021) Enzyme evolution for industrial biocatalytic cascades. Current Opinion in Biotechnology 69, pages 182-190.
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Niki R. Patel, Mark A. Huffman, Xiao Wang, Bangwei Ding, Mark McLaughlin, Justin A. Newman, Teresa Andreani, Kevin M. Maloney, Heather C. Johnson & Aaron M. Whittaker. (2020) Five‐Step Enantioselective Synthesis of Islatravir via Asymmetric Ketone Alkynylation and an Ozonolysis Cascade. Chemistry – A European Journal 26:62, pages 14118-14123.
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Niki R. Patel, Christopher C. Nawrat, Mark McLaughlin, Yingju Xu, Mark A. Huffman, Hao Yang, Hongming Li, Aaron M. Whittaker, Teresa Andreani, François Lévesque, Anna Fryszkowska, Andrew Brunskill, David M. Tschaen & Kevin M. Maloney. (2020) Synthesis of Islatravir Enabled by a Catalytic, Enantioselective Alkynylation of a Ketone. Organic Letters 22:12, pages 4659-4664.
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Keykavous Parang, Naglaa Salem El-Sayed, Assad J. Kazeminy & Rakesh K. Tiwari. (2020) Comparative Antiviral Activity of Remdesivir and Anti-HIV Nucleoside Analogs against Human Coronavirus 229E (HCoV-229E). Molecules 25:10, pages 2343.
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Christopher C. Nawrat, Aaron M. Whittaker, Mark A. Huffman, Mark McLaughlin, Ryan D. Cohen, Teresa Andreani, Bangwei Ding, Hongming Li, Mark Weisel & David M. Tschaen. (2020) Nine-Step Stereoselective Synthesis of Islatravir from Deoxyribose. Organic Letters 22:6, pages 2167-2172.
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Mark A. Huffman, Anna Fryszkowska, Oscar Alvizo, Margie Borra-Garske, Kevin R. Campos, Keith A. CanadaPaul N. Devine, Da Duan, Jacob H. Forstater, Shane T. Grosser, Holst M. Halsey, Gregory J. Hughes, Junyong Jo, Leo A. Joyce, Joshua N. Kolev, Jack LiangKevin M. Maloney, Benjamin F. Mann, Nicholas M. MarshallMark McLaughlinJeffrey C. Moore, Grant S. Murphy, Christopher C. Nawrat, Jovana Nazor, Scott NovickNiki R. Patel, Agustina Rodriguez-Granillo, Sandra A. Robaire, Edward C. Sherer, Matthew D. Truppo, Aaron M. WhittakerDeeptak Verma, Li XiaoYingju Xu & Hao Yang. (2019) Design of an in vitro biocatalytic cascade for the manufacture of islatravir. Science 366:6470, pages 1255-1259.
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I. V. Mineyeva. (2019) Functionalized 2-Substituted Allyl Bromides in the Barbier Allylation of (R)-2,3-O-Isopropylideneglyceraldehyde. Synthesis of the C8–C17, C8–C18, and C5–C17 Building Blocks of Laulimalides and Their Synthetic Analogs. Russian Journal of Organic Chemistry 55:4, pages 530-539.
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Mark McLaughlin, Jongrock Kong, Kevin M. Belyk, Billy Chen, Andrew W. Gibson, Stephen P. Keen, David R. Lieberman, Erika M. Milczek, Jeffrey C. Moore, David Murray, Feng Peng, Ji Qi, Robert A. Reamer, Zhiguo J. Song, Lushi Tan, Lin Wang & Michael J. Williams. (2017) Enantioselective Synthesis of 4′-Ethynyl-2-fluoro-2′-deoxyadenosine (EFdA) via Enzymatic Desymmetrization. Organic Letters 19:4, pages 926-929.
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Kei Fukuyama, Hiroshi Ohrui & Shigefumi Kuwahara. (2015) Synthesis of EFdA via a Diastereoselective Aldol Reaction of a Protected 3-Keto Furanose. Organic Letters 17:4, pages 828-831.
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