Structure and conformation of 3′-azido-3′-deoxythymidine (AZT), an inhibitor of the HIV (AIDS) virus
3′-Azido-3′-deoxythymidine (AZT), an inhibitor of HIV (human immunodeficiency virus) replication, was recently found to improve the condition of patients suffering from AIDS (acquired immunodeficiency syndrome) or ARC (AIDS-related complex). An X-ray analysis of AZT was undertaken in order to determ...
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| Veröffentlicht in: | Canadian journal of chemistry 1987-09, Vol.65 (9), p.2135-2139 |
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| creator | Birnbaum, George I Giziewicz, Jerzy Gabe, Eric J Lin, Tai-Shun Prusoff, William H |
| description | 3′-Azido-3′-deoxythymidine (AZT), an inhibitor of HIV (human immunodeficiency virus) replication, was recently found to improve the condition of patients suffering from AIDS (acquired immunodeficiency syndrome) or ARC (AIDS-related complex). An X-ray analysis of AZT was undertaken in order to determine the three-dimensional structure of this thymidine analogue. The crystals belong to the monoclinic space group P2
1
and the cell dimensions are a = 5.6282(4), b = 12.0130(7), c = 17.5072(10) Å, β = 95.946(5)°. The structure was determined by direct methods and refined to R = 0.028 for 2029 observed reflections. Two crystallographically independent molecules were found in the asymmetric unit. One of them, molecule A, adopts a conformation which is fairly common in nucleosides, viz. a C2′ endo/C3′ exo pucker of the furanose ring and a glycosidic torsion angle χ
CN
= 53.4°. However, the conformation of molecule B is highly unusual. The sugar ring pucker is C3′ exo/C4′ endo and χ
CN
= 2.3°. This high-energy conformation may represent the biologically active form of AZT. Its determination may therefore assist in the design of other inhibitors of HIV. |
| doi_str_mv | 10.1139/v87-356 |
| format | Article |
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1
and the cell dimensions are a = 5.6282(4), b = 12.0130(7), c = 17.5072(10) Å, β = 95.946(5)°. The structure was determined by direct methods and refined to R = 0.028 for 2029 observed reflections. Two crystallographically independent molecules were found in the asymmetric unit. One of them, molecule A, adopts a conformation which is fairly common in nucleosides, viz. a C2′ endo/C3′ exo pucker of the furanose ring and a glycosidic torsion angle χ
CN
= 53.4°. However, the conformation of molecule B is highly unusual. The sugar ring pucker is C3′ exo/C4′ endo and χ
CN
= 2.3°. This high-energy conformation may represent the biologically active form of AZT. Its determination may therefore assist in the design of other inhibitors of HIV.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v87-356</identifier><identifier>CODEN: CJCHAG</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><subject>Condensed matter: structure, mechanical and thermal properties ; Exact sciences and technology ; Heterocyclic compounds ; Organic compounds ; Physics ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids</subject><ispartof>Canadian journal of chemistry, 1987-09, Vol.65 (9), p.2135-2139</ispartof><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c349t-3f86e670a46b36d617c48cb50133f50ef48e3b731fc4fadec42e02fceca428703</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://cdnsciencepub.com/doi/pdf/10.1139/v87-356$$EPDF$$P50$$Gnrcresearch$$H</linktopdf><linktohtml>$$Uhttps://cdnsciencepub.com/doi/full/10.1139/v87-356$$EHTML$$P50$$Gnrcresearch$$H</linktohtml><link.rule.ids>314,776,780,2919,27901,27902,64401,65207</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7710945$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Birnbaum, George I</creatorcontrib><creatorcontrib>Giziewicz, Jerzy</creatorcontrib><creatorcontrib>Gabe, Eric J</creatorcontrib><creatorcontrib>Lin, Tai-Shun</creatorcontrib><creatorcontrib>Prusoff, William H</creatorcontrib><title>Structure and conformation of 3′-azido-3′-deoxythymidine (AZT), an inhibitor of the HIV (AIDS) virus</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>3′-Azido-3′-deoxythymidine (AZT), an inhibitor of HIV (human immunodeficiency virus) replication, was recently found to improve the condition of patients suffering from AIDS (acquired immunodeficiency syndrome) or ARC (AIDS-related complex). An X-ray analysis of AZT was undertaken in order to determine the three-dimensional structure of this thymidine analogue. The crystals belong to the monoclinic space group P2
1
and the cell dimensions are a = 5.6282(4), b = 12.0130(7), c = 17.5072(10) Å, β = 95.946(5)°. The structure was determined by direct methods and refined to R = 0.028 for 2029 observed reflections. Two crystallographically independent molecules were found in the asymmetric unit. One of them, molecule A, adopts a conformation which is fairly common in nucleosides, viz. a C2′ endo/C3′ exo pucker of the furanose ring and a glycosidic torsion angle χ
CN
= 53.4°. However, the conformation of molecule B is highly unusual. The sugar ring pucker is C3′ exo/C4′ endo and χ
CN
= 2.3°. This high-energy conformation may represent the biologically active form of AZT. Its determination may therefore assist in the design of other inhibitors of HIV.</description><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNp90LtOwzAUBmALgUQpiFfIgApFGOzYuY1VubQSEkMLA0vkOMeKURIXO6koE8_EI_EkpLRig-n4yN_5hx-hY0ouKWXJ1TKOMAvCHdSjPCaY-QndRT1CSIw54f4-OnDupVsj4gc9VMwa28qmteCJOvekqZWxlWi0qT2jPPb18YnFu84N_nnmYN5WTbGqdK5r8M5Gz_PhRXfp6brQmW6MXV81BXiT6VP3Pb2eDb2ltq07RHtKlA6OtrOPHm9v5uMJvn-4m45H91gynjSYqTiEMCKChxkL85BGkscyCwhlTAUEFI-BZRGjSnIlcpDcB-IrCVJwP44I66PBJndhzWsLrkkr7SSUpajBtC6lPCEsJLyDpxsorXHOgkoXVlfCrlJK0nWTaddk2jXZyZNtpHBSlMqKWmr3y6OIkoQHHTvfsNpKCw6ElcU_mYO_8Rali1yxb6lcjwg</recordid><startdate>19870901</startdate><enddate>19870901</enddate><creator>Birnbaum, George I</creator><creator>Giziewicz, Jerzy</creator><creator>Gabe, Eric J</creator><creator>Lin, Tai-Shun</creator><creator>Prusoff, William H</creator><general>NRC Research Press</general><general>National Research Council of Canada</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope></search><sort><creationdate>19870901</creationdate><title>Structure and conformation of 3′-azido-3′-deoxythymidine (AZT), an inhibitor of the HIV (AIDS) virus</title><author>Birnbaum, George I ; Giziewicz, Jerzy ; Gabe, Eric J ; Lin, Tai-Shun ; Prusoff, William H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c349t-3f86e670a46b36d617c48cb50133f50ef48e3b731fc4fadec42e02fceca428703</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Birnbaum, George I</creatorcontrib><creatorcontrib>Giziewicz, Jerzy</creatorcontrib><creatorcontrib>Gabe, Eric J</creatorcontrib><creatorcontrib>Lin, Tai-Shun</creatorcontrib><creatorcontrib>Prusoff, William H</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Birnbaum, George I</au><au>Giziewicz, Jerzy</au><au>Gabe, Eric J</au><au>Lin, Tai-Shun</au><au>Prusoff, William H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure and conformation of 3′-azido-3′-deoxythymidine (AZT), an inhibitor of the HIV (AIDS) virus</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1987-09-01</date><risdate>1987</risdate><volume>65</volume><issue>9</issue><spage>2135</spage><epage>2139</epage><pages>2135-2139</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><coden>CJCHAG</coden><abstract>3′-Azido-3′-deoxythymidine (AZT), an inhibitor of HIV (human immunodeficiency virus) replication, was recently found to improve the condition of patients suffering from AIDS (acquired immunodeficiency syndrome) or ARC (AIDS-related complex). An X-ray analysis of AZT was undertaken in order to determine the three-dimensional structure of this thymidine analogue. The crystals belong to the monoclinic space group P2
1
and the cell dimensions are a = 5.6282(4), b = 12.0130(7), c = 17.5072(10) Å, β = 95.946(5)°. The structure was determined by direct methods and refined to R = 0.028 for 2029 observed reflections. Two crystallographically independent molecules were found in the asymmetric unit. One of them, molecule A, adopts a conformation which is fairly common in nucleosides, viz. a C2′ endo/C3′ exo pucker of the furanose ring and a glycosidic torsion angle χ
CN
= 53.4°. However, the conformation of molecule B is highly unusual. The sugar ring pucker is C3′ exo/C4′ endo and χ
CN
= 2.3°. This high-energy conformation may represent the biologically active form of AZT. Its determination may therefore assist in the design of other inhibitors of HIV.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v87-356</doi><tpages>5</tpages></addata></record> |
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| subjects | Condensed matter: structure, mechanical and thermal properties Exact sciences and technology Heterocyclic compounds Organic compounds Physics Structure of solids and liquids crystallography Structure of specific crystalline solids |
| title | Structure and conformation of 3′-azido-3′-deoxythymidine (AZT), an inhibitor of the HIV (AIDS) virus |
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