Racemic diastereoisomers of 1-amino-2-hydroxycyclopentanecarboxylic acid
The synthesis and characterization of the two diastereoisomeric forms of 1-amino-2-hydroxycyclopentanecarboxylic acid have been accomplished. A previously reported synthesis produced a racemic mixture of the threonine analog trans-2-hydroxy-1-aminocyclopentanecarboxylic acid (trans with respect to t...
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| Veröffentlicht in: | Journal of medicinal chemistry 1976-02, Vol.19 (2), p.342-344 |
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| container_end_page | 344 |
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| container_issue | 2 |
| container_start_page | 342 |
| container_title | Journal of medicinal chemistry |
| container_volume | 19 |
| creator | Gaitanopoulos, Dimitri E Nash, James Dunn, Danny L Skinner, Charles G |
| description | The synthesis and characterization of the two diastereoisomeric forms of 1-amino-2-hydroxycyclopentanecarboxylic acid have been accomplished. A previously reported synthesis produced a racemic mixture of the threonine analog trans-2-hydroxy-1-aminocyclopentanecarboxylic acid (trans with respect to the hydroxy and carboxyl group). The alternate allothreonine analog was produced by conversion of cyclopentene oxide to trans-2-methoxycyclopentanol, followed by oxidation to 2-methoxycyclopentanone and conversion to a hydantoin. Fractional crystallization of the hydantoin sample, followed by hydrolysis, produced cis-2-hydroxy-1-aminocyclopentanecarboxylic acid (cis with respect to the hydroxy and carboxyl group) in high purity. Neither of the isomeric forms significantly inhibited the growth of the bacterial strains examined nor were they effective in inhibiting Jensen sarcoma cells in tissue culture. |
| doi_str_mv | 10.1021/jm00224a031 |
| format | Article |
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A previously reported synthesis produced a racemic mixture of the threonine analog trans-2-hydroxy-1-aminocyclopentanecarboxylic acid (trans with respect to the hydroxy and carboxyl group). The alternate allothreonine analog was produced by conversion of cyclopentene oxide to trans-2-methoxycyclopentanol, followed by oxidation to 2-methoxycyclopentanone and conversion to a hydantoin. Fractional crystallization of the hydantoin sample, followed by hydrolysis, produced cis-2-hydroxy-1-aminocyclopentanecarboxylic acid (cis with respect to the hydroxy and carboxyl group) in high purity. Neither of the isomeric forms significantly inhibited the growth of the bacterial strains examined nor were they effective in inhibiting Jensen sarcoma cells in tissue culture.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00224a031</identifier><identifier>PMID: 814238</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amino Acids - chemical synthesis ; Amino Acids - pharmacology ; Animals ; Cyclopentanes - chemical synthesis ; Cyclopentanes - pharmacology ; Enterococcus faecalis - drug effects ; Escherichia coli - drug effects ; Lactobacillus - drug effects ; Leuconostoc - drug effects ; Microbial Sensitivity Tests ; Models, Molecular ; Molecular Conformation ; Sarcoma, Experimental - metabolism ; Stereoisomerism</subject><ispartof>Journal of medicinal chemistry, 1976-02, Vol.19 (2), p.342-344</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a353t-2b2743302c30a0982168c9c4b1200dd163ace0f36628a256be707c67855779173</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00224a031$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00224a031$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/814238$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gaitanopoulos, Dimitri E</creatorcontrib><creatorcontrib>Nash, James</creatorcontrib><creatorcontrib>Dunn, Danny L</creatorcontrib><creatorcontrib>Skinner, Charles G</creatorcontrib><title>Racemic diastereoisomers of 1-amino-2-hydroxycyclopentanecarboxylic acid</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The synthesis and characterization of the two diastereoisomeric forms of 1-amino-2-hydroxycyclopentanecarboxylic acid have been accomplished. A previously reported synthesis produced a racemic mixture of the threonine analog trans-2-hydroxy-1-aminocyclopentanecarboxylic acid (trans with respect to the hydroxy and carboxyl group). The alternate allothreonine analog was produced by conversion of cyclopentene oxide to trans-2-methoxycyclopentanol, followed by oxidation to 2-methoxycyclopentanone and conversion to a hydantoin. Fractional crystallization of the hydantoin sample, followed by hydrolysis, produced cis-2-hydroxy-1-aminocyclopentanecarboxylic acid (cis with respect to the hydroxy and carboxyl group) in high purity. Neither of the isomeric forms significantly inhibited the growth of the bacterial strains examined nor were they effective in inhibiting Jensen sarcoma cells in tissue culture.</description><subject>Amino Acids - chemical synthesis</subject><subject>Amino Acids - pharmacology</subject><subject>Animals</subject><subject>Cyclopentanes - chemical synthesis</subject><subject>Cyclopentanes - pharmacology</subject><subject>Enterococcus faecalis - drug effects</subject><subject>Escherichia coli - drug effects</subject><subject>Lactobacillus - drug effects</subject><subject>Leuconostoc - drug effects</subject><subject>Microbial Sensitivity Tests</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Sarcoma, Experimental - metabolism</subject><subject>Stereoisomerism</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1976</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkLtPwzAQhy3EqxQmVoZOMCDD-ZzEzogqSpF4FCiz5TiuSEnqYrdS-9_jKlXFwHTS_b576CPknMENA2S30wYAMdHA2R7psBSBJhKSfdLZ9ClmyI_JSQhTgIggPyKHkiXIZYcM37WxTWV6ZaXDwnrrquAa60PPTXqM6qaaOYr0a116t1qbtand3M4WemaN9kVs1XFWm6o8JQcTXQd7tq1d8jm4H_eH9On14bF_90Q1T_mCYoEi4RzQcNCQS2SZNLlJCoYAZckyHv-BCc8ylBrTrLAChMmETFMhciZ4l1y2e-fe_SxtWKimCsbWdXzJLYOSHPOcMx7B6xY03oXg7UTNfdVov1YM1Eab-qMt0hfbtcuiseWObT3FmLZxFSWtdqn23yoTXKRqPPpQo2d4G6QvUo0if9Xy2gQ1dUs_i07-PfwL05yBwQ</recordid><startdate>19760201</startdate><enddate>19760201</enddate><creator>Gaitanopoulos, Dimitri E</creator><creator>Nash, James</creator><creator>Dunn, Danny L</creator><creator>Skinner, Charles G</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19760201</creationdate><title>Racemic diastereoisomers of 1-amino-2-hydroxycyclopentanecarboxylic acid</title><author>Gaitanopoulos, Dimitri E ; Nash, James ; Dunn, Danny L ; Skinner, Charles G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a353t-2b2743302c30a0982168c9c4b1200dd163ace0f36628a256be707c67855779173</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1976</creationdate><topic>Amino Acids - chemical synthesis</topic><topic>Amino Acids - pharmacology</topic><topic>Animals</topic><topic>Cyclopentanes - chemical synthesis</topic><topic>Cyclopentanes - pharmacology</topic><topic>Enterococcus faecalis - drug effects</topic><topic>Escherichia coli - drug effects</topic><topic>Lactobacillus - drug effects</topic><topic>Leuconostoc - drug effects</topic><topic>Microbial Sensitivity Tests</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Sarcoma, Experimental - metabolism</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gaitanopoulos, Dimitri E</creatorcontrib><creatorcontrib>Nash, James</creatorcontrib><creatorcontrib>Dunn, Danny L</creatorcontrib><creatorcontrib>Skinner, Charles G</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gaitanopoulos, Dimitri E</au><au>Nash, James</au><au>Dunn, Danny L</au><au>Skinner, Charles G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Racemic diastereoisomers of 1-amino-2-hydroxycyclopentanecarboxylic acid</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1976-02-01</date><risdate>1976</risdate><volume>19</volume><issue>2</issue><spage>342</spage><epage>344</epage><pages>342-344</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>The synthesis and characterization of the two diastereoisomeric forms of 1-amino-2-hydroxycyclopentanecarboxylic acid have been accomplished. A previously reported synthesis produced a racemic mixture of the threonine analog trans-2-hydroxy-1-aminocyclopentanecarboxylic acid (trans with respect to the hydroxy and carboxyl group). The alternate allothreonine analog was produced by conversion of cyclopentene oxide to trans-2-methoxycyclopentanol, followed by oxidation to 2-methoxycyclopentanone and conversion to a hydantoin. Fractional crystallization of the hydantoin sample, followed by hydrolysis, produced cis-2-hydroxy-1-aminocyclopentanecarboxylic acid (cis with respect to the hydroxy and carboxyl group) in high purity. Neither of the isomeric forms significantly inhibited the growth of the bacterial strains examined nor were they effective in inhibiting Jensen sarcoma cells in tissue culture.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>814238</pmid><doi>10.1021/jm00224a031</doi><tpages>3</tpages></addata></record> |
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| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1976-02, Vol.19 (2), p.342-344 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Amino Acids - chemical synthesis Amino Acids - pharmacology Animals Cyclopentanes - chemical synthesis Cyclopentanes - pharmacology Enterococcus faecalis - drug effects Escherichia coli - drug effects Lactobacillus - drug effects Leuconostoc - drug effects Microbial Sensitivity Tests Models, Molecular Molecular Conformation Sarcoma, Experimental - metabolism Stereoisomerism |
| title | Racemic diastereoisomers of 1-amino-2-hydroxycyclopentanecarboxylic acid |
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