Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle

Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle

The selective recruitment of oligosaccharides, or even simple sugars, in water solvent is an unsolved molecular recognition problem. Structure-guided, electrostatic redesign led to a significant increase in the affinity of a β-peptide “borono-bundle” for simple sugars in neutral aqueous solution. Th...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2015-10, Vol.17 (19), p.4718-4721
Hauptverfasser: Melicher, Michael S, Walker, Allison S, Shen, John, Miller, Scott J, Schepartz, Alanna
Format: Artikel
Sprache:eng
Schlagworte:
Carbohydrates - chemistry
Fructose - chemistry
Glucose - chemistry
Molecular Structure
Oligosaccharides - chemistry
Peptides - chemistry
Solvents
Sorbitol - chemistry
Static Electricity
Thermodynamics
Water - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4721
container_issue 19
container_start_page 4718
container_title Organic letters
container_volume 17
creator Melicher, Michael S
Walker, Allison S
Shen, John
Miller, Scott J
Schepartz, Alanna
description The selective recruitment of oligosaccharides, or even simple sugars, in water solvent is an unsolved molecular recognition problem. Structure-guided, electrostatic redesign led to a significant increase in the affinity of a β-peptide “borono-bundle” for simple sugars in neutral aqueous solution. The affinity for fructose (663 M–1) in water should allow its recruitment to the bundle surface for selective catalysis, and future work will focus in this direction.
doi_str_mv 10.1021/acs.orglett.5b02187
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1718907769</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1718907769</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-91105bf2566b122562f8e984ed6459dce0f639bd2bf12ca34c4e28e140ee44913</originalsourceid><addsrcrecordid>eNp9kEFOwzAURC0EoqVwAiTkJZu0tpM4yRKqApUqgRCIZeQ4P62rxCm2A-qOK3AVDsIhOAmuWrpk9a3RzFjzEDqnZEgJoyMh7bA18xqcG8aFV9LkAPVpzMIgITE73L856aETa5eEUK9kx6jHeJhwkvA-EtNmZdo3KPFYmKJdrEsjHOBHkO1cK6dajZXGL14z-F25BRYaT2qQzrTWCaekqOs1nuiF0NKXfH_9fHw-wMqpEvB1p8saTtFRJWoLZ7s7QM83k6fxXTC7v52Or2aBCKPYBRmlJC4qFnNeUOYPq1LI0ghKHsVZKYFUPMyKkhUVZdJnZAQsBRoRgCjKaDhAl9tev-e1A-vyRlkJdS00tJ3NaULTjCQJz7w13FqlX2ENVPnKqEaYdU5JvmGbe7b5jm2-Y-tTF7sPuqKBcp_5g-kNo61hk162ndF-77-Vv0skirU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1718907769</pqid></control><display><type>article</type><title>Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Melicher, Michael S ; Walker, Allison S ; Shen, John ; Miller, Scott J ; Schepartz, Alanna</creator><creatorcontrib>Melicher, Michael S ; Walker, Allison S ; Shen, John ; Miller, Scott J ; Schepartz, Alanna</creatorcontrib><description>The selective recruitment of oligosaccharides, or even simple sugars, in water solvent is an unsolved molecular recognition problem. Structure-guided, electrostatic redesign led to a significant increase in the affinity of a β-peptide “borono-bundle” for simple sugars in neutral aqueous solution. The affinity for fructose (663 M–1) in water should allow its recruitment to the bundle surface for selective catalysis, and future work will focus in this direction.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.5b02187</identifier><identifier>PMID: 26376076</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Carbohydrates - chemistry ; Fructose - chemistry ; Glucose - chemistry ; Molecular Structure ; Oligosaccharides - chemistry ; Peptides - chemistry ; Solvents ; Sorbitol - chemistry ; Static Electricity ; Thermodynamics ; Water - chemistry</subject><ispartof>Organic letters, 2015-10, Vol.17 (19), p.4718-4721</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-91105bf2566b122562f8e984ed6459dce0f639bd2bf12ca34c4e28e140ee44913</citedby><cites>FETCH-LOGICAL-a345t-91105bf2566b122562f8e984ed6459dce0f639bd2bf12ca34c4e28e140ee44913</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.5b02187$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.5b02187$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26376076$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Melicher, Michael S</creatorcontrib><creatorcontrib>Walker, Allison S</creatorcontrib><creatorcontrib>Shen, John</creatorcontrib><creatorcontrib>Miller, Scott J</creatorcontrib><creatorcontrib>Schepartz, Alanna</creatorcontrib><title>Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The selective recruitment of oligosaccharides, or even simple sugars, in water solvent is an unsolved molecular recognition problem. Structure-guided, electrostatic redesign led to a significant increase in the affinity of a β-peptide “borono-bundle” for simple sugars in neutral aqueous solution. The affinity for fructose (663 M–1) in water should allow its recruitment to the bundle surface for selective catalysis, and future work will focus in this direction.</description><subject>Carbohydrates - chemistry</subject><subject>Fructose - chemistry</subject><subject>Glucose - chemistry</subject><subject>Molecular Structure</subject><subject>Oligosaccharides - chemistry</subject><subject>Peptides - chemistry</subject><subject>Solvents</subject><subject>Sorbitol - chemistry</subject><subject>Static Electricity</subject><subject>Thermodynamics</subject><subject>Water - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEFOwzAURC0EoqVwAiTkJZu0tpM4yRKqApUqgRCIZeQ4P62rxCm2A-qOK3AVDsIhOAmuWrpk9a3RzFjzEDqnZEgJoyMh7bA18xqcG8aFV9LkAPVpzMIgITE73L856aETa5eEUK9kx6jHeJhwkvA-EtNmZdo3KPFYmKJdrEsjHOBHkO1cK6dajZXGL14z-F25BRYaT2qQzrTWCaekqOs1nuiF0NKXfH_9fHw-wMqpEvB1p8saTtFRJWoLZ7s7QM83k6fxXTC7v52Or2aBCKPYBRmlJC4qFnNeUOYPq1LI0ghKHsVZKYFUPMyKkhUVZdJnZAQsBRoRgCjKaDhAl9tev-e1A-vyRlkJdS00tJ3NaULTjCQJz7w13FqlX2ENVPnKqEaYdU5JvmGbe7b5jm2-Y-tTF7sPuqKBcp_5g-kNo61hk162ndF-77-Vv0skirU</recordid><startdate>20151002</startdate><enddate>20151002</enddate><creator>Melicher, Michael S</creator><creator>Walker, Allison S</creator><creator>Shen, John</creator><creator>Miller, Scott J</creator><creator>Schepartz, Alanna</creator><general>American Chemical Society</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>20151002</creationdate><title>Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle</title><author>Melicher, Michael S ; Walker, Allison S ; Shen, John ; Miller, Scott J ; Schepartz, Alanna</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-91105bf2566b122562f8e984ed6459dce0f639bd2bf12ca34c4e28e140ee44913</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Carbohydrates - chemistry</topic><topic>Fructose - chemistry</topic><topic>Glucose - chemistry</topic><topic>Molecular Structure</topic><topic>Oligosaccharides - chemistry</topic><topic>Peptides - chemistry</topic><topic>Solvents</topic><topic>Sorbitol - chemistry</topic><topic>Static Electricity</topic><topic>Thermodynamics</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Melicher, Michael S</creatorcontrib><creatorcontrib>Walker, Allison S</creatorcontrib><creatorcontrib>Shen, John</creatorcontrib><creatorcontrib>Miller, Scott J</creatorcontrib><creatorcontrib>Schepartz, Alanna</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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Melicher, Michael S</au><au>Walker, Allison S</au><au>Shen, John</au><au>Miller, Scott J</au><au>Schepartz, Alanna</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2015-10-02</date><risdate>2015</risdate><volume>17</volume><issue>19</issue><spage>4718</spage><epage>4721</epage><pages>4718-4721</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The selective recruitment of oligosaccharides, or even simple sugars, in water solvent is an unsolved molecular recognition problem. Structure-guided, electrostatic redesign led to a significant increase in the affinity of a β-peptide “borono-bundle” for simple sugars in neutral aqueous solution. The affinity for fructose (663 M–1) in water should allow its recruitment to the bundle surface for selective catalysis, and future work will focus in this direction.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26376076</pmid><doi>10.1021/acs.orglett.5b02187</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2015-10, Vol.17 (19), p.4718-4721
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_1718907769
source MEDLINE; American Chemical Society Journals
subjects Carbohydrates - chemistry
Fructose - chemistry
Glucose - chemistry
Molecular Structure
Oligosaccharides - chemistry
Peptides - chemistry
Solvents
Sorbitol - chemistry
Static Electricity
Thermodynamics
Water - chemistry
title Improved Carbohydrate Recognition in Water with an Electrostatically Enhanced β‑Peptide Bundle
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T11%3A49%3A18IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Improved%20Carbohydrate%20Recognition%20in%20Water%20with%20an%20Electrostatically%20Enhanced%20%CE%B2%E2%80%91Peptide%20Bundle&rft.jtitle=Organic%20letters&rft.au=Melicher,%20Michael%20S&rft.date=2015-10-02&rft.volume=17&rft.issue=19&rft.spage=4718&rft.epage=4721&rft.pages=4718-4721&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.5b02187&rft_dat=%3Cproquest_cross%3E1718907769%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1718907769&rft_id=info:pmid/26376076&rfr_iscdi=true