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Synthesis of octahydropyrano[3,2- b]pyrrole-2-carboxylic acid derivatives from d-mannose
Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products aeruginosins. Many compounds in the aeruginosin family exhibit inhibition...
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Published in: | Carbohydrate research 2008-07, Vol.343 (10), p.1743-1753 |
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container_title | Carbohydrate research |
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creator | Ella-Menye, Jean-Rene Nie, Xiaoping Wang, Guijun |
description | Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products aeruginosins. Many compounds in the aeruginosin family exhibit inhibition activities toward serine proteases including thrombin and trypsin. The unique Choi structure is the common feature of this family of oligopeptides and this motif is important for their observed biological activities. To better understand the influence of the stereochemistry of the Choi core structure on the inhibition activities, we have previously synthesized ring-oxygenated variants from glucose. The preparation of octahydro-pyrano[3,2-
b]pyrrole 2-carboxylic acids from
d-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules. |
doi_str_mv | 10.1016/j.carres.2008.03.017 |
format | article |
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b]pyrrole 2-carboxylic acids from
d-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules.</description><subject>Aerguginosin</subject><subject>Bridged Bicyclo Compounds - chemical synthesis</subject><subject>Mannose - chemistry</subject><subject>Octahydroindole 2-carboxylic acid</subject><subject>Pyrans - chemical synthesis</subject><subject>Pyrroles - chemical synthesis</subject><subject>Rigid conformation</subject><subject>Thrombin inhibitor</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNp9kMFqGzEQhkVIiV2nbxDCnnKKttJqV5IvgRKStGDooQkYShFaaYRldleOtDbZt6-MDb31MsMw_8w_8yF0Q0lJCeVft6XRMUIqK0JkSVhJqLhAcyoFw3XF15doTnIH84o2M_Q5pW0uCRf8Cs2orBkTbDlH61_TMG4g-VQEVwQz6s1kY9hNUQ_hN7uvcNH-yVUMHeAKZ8s2fEydN4U23hYWoj_o0R8gFS6GvrC418MQElyjT053Cb6c8wK9PT-9Pn7Hq58vPx6_rbDJR45YMgeN1k5DKzixDVk6R7SWOTZUykpI0TYgOa8FqwU0jrOWmSUXonWyJpYt0N1p7y6G9z2kUfU-Geg6PUDYJ8WXVZWd6iysT0ITQ0oRnNpF3-s4KUrUkajaqhNRdSSqCFOZaB67Pe_ftz3Yf0NnhFnwcBJA_vLgIapkPAwGrI9gRmWD_7_DX77dihw</recordid><startdate>20080721</startdate><enddate>20080721</enddate><creator>Ella-Menye, Jean-Rene</creator><creator>Nie, Xiaoping</creator><creator>Wang, Guijun</creator><general>Elsevier Ltd</general><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>20080721</creationdate><title>Synthesis of octahydropyrano[3,2- b]pyrrole-2-carboxylic acid derivatives from d-mannose</title><author>Ella-Menye, Jean-Rene ; Nie, Xiaoping ; Wang, Guijun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c426t-83fe5aafaeb760d509ff0aa8ff051882787b5e86647347e5f63b3c9677bf840d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Aerguginosin</topic><topic>Bridged Bicyclo Compounds - chemical synthesis</topic><topic>Mannose - chemistry</topic><topic>Octahydroindole 2-carboxylic acid</topic><topic>Pyrans - chemical synthesis</topic><topic>Pyrroles - chemical synthesis</topic><topic>Rigid conformation</topic><topic>Thrombin inhibitor</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ella-Menye, Jean-Rene</creatorcontrib><creatorcontrib>Nie, Xiaoping</creatorcontrib><creatorcontrib>Wang, Guijun</creatorcontrib><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>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ella-Menye, Jean-Rene</au><au>Nie, Xiaoping</au><au>Wang, Guijun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of octahydropyrano[3,2- b]pyrrole-2-carboxylic acid derivatives from d-mannose</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2008-07-21</date><risdate>2008</risdate><volume>343</volume><issue>10</issue><spage>1743</spage><epage>1753</epage><pages>1743-1753</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products aeruginosins. Many compounds in the aeruginosin family exhibit inhibition activities toward serine proteases including thrombin and trypsin. The unique Choi structure is the common feature of this family of oligopeptides and this motif is important for their observed biological activities. To better understand the influence of the stereochemistry of the Choi core structure on the inhibition activities, we have previously synthesized ring-oxygenated variants from glucose. The preparation of octahydro-pyrano[3,2-
b]pyrrole 2-carboxylic acids from
d-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>18433739</pmid><doi>10.1016/j.carres.2008.03.017</doi><tpages>11</tpages></addata></record> |
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subjects | Aerguginosin Bridged Bicyclo Compounds - chemical synthesis Mannose - chemistry Octahydroindole 2-carboxylic acid Pyrans - chemical synthesis Pyrroles - chemical synthesis Rigid conformation Thrombin inhibitor |
title | Synthesis of octahydropyrano[3,2- b]pyrrole-2-carboxylic acid derivatives from d-mannose |
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