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Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles
ABSTRACT Our recently discovered, selective, on‐resin route to N(τ)‐alkylated imidazolium‐containing histidine residues affords new strategies for peptide mimetic design. In this, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups...
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| Published in: | Biopolymers 2015-11, Vol.104 (6), p.663-673 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
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| cited_by | cdi_FETCH-LOGICAL-c6128-d822f705b305bc808ce691aa89a3f331c38d393802b631edc9519bfd0a9c49643 |
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| cites | cdi_FETCH-LOGICAL-c6128-d822f705b305bc808ce691aa89a3f331c38d393802b631edc9519bfd0a9c49643 |
| container_end_page | 673 |
| container_issue | 6 |
| container_start_page | 663 |
| container_title | Biopolymers |
| container_volume | 104 |
| creator | Qian, Wen-Jian Park, Jung-Eun Grant, Robert Lai, Christopher C. Kelley, James A. Yaffe, Michael B. Lee, Kyung S. Burke Jr, Terrence R. |
| description | ABSTRACT
Our recently discovered, selective, on‐resin route to N(τ)‐alkylated imidazolium‐containing histidine residues affords new strategies for peptide mimetic design. In this, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups serve as ring‐forming junctions. Interestingly, these cationic moieties subsequently serve to charge‐mask the phosphoamino acid group that directed their formation. Neighbor‐directed histidine N(τ)‐alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 104: 663–673, 2015. |
| doi_str_mv | 10.1002/bip.22698 |
| format | article |
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Our recently discovered, selective, on‐resin route to N(τ)‐alkylated imidazolium‐containing histidine residues affords new strategies for peptide mimetic design. In this, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups serve as ring‐forming junctions. Interestingly, these cationic moieties subsequently serve to charge‐mask the phosphoamino acid group that directed their formation. Neighbor‐directed histidine N(τ)‐alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 104: 663–673, 2015.</description><identifier>ISSN: 0006-3525</identifier><identifier>ISSN: 1097-0282</identifier><identifier>EISSN: 1097-0282</identifier><identifier>DOI: 10.1002/bip.22698</identifier><identifier>PMID: 26152807</identifier><language>eng</language><publisher>United States: Blackwell Publishing Ltd</publisher><subject>Alkylation ; Biology ; Biopolymers ; Cationic ; cationic dialkyl histidine ; crystal structure ; Crystallography, X-Ray ; Formations ; Histidine ; Histidine - chemistry ; Imidazoles - chemistry ; Macrocyclic compounds ; Macrocyclic Compounds - chemistry ; peptide macrocycles ; peptide macrocycles, phosphopeptides ; Peptides ; phosphopeptides ; Phosphopeptides - chemistry ; PLk1 ; polo kinase ; polo-box domain ; Residues ; Strategy</subject><ispartof>Biopolymers, 2015-11, Vol.104 (6), p.663-673</ispartof><rights>2015 Wiley Periodicals, Inc.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6128-d822f705b305bc808ce691aa89a3f331c38d393802b631edc9519bfd0a9c49643</citedby><cites>FETCH-LOGICAL-c6128-d822f705b305bc808ce691aa89a3f331c38d393802b631edc9519bfd0a9c49643</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26152807$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/1228107$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Qian, Wen-Jian</creatorcontrib><creatorcontrib>Park, Jung-Eun</creatorcontrib><creatorcontrib>Grant, Robert</creatorcontrib><creatorcontrib>Lai, Christopher C.</creatorcontrib><creatorcontrib>Kelley, James A.</creatorcontrib><creatorcontrib>Yaffe, Michael B.</creatorcontrib><creatorcontrib>Lee, Kyung S.</creatorcontrib><creatorcontrib>Burke Jr, Terrence R.</creatorcontrib><creatorcontrib>Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)</creatorcontrib><title>Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles</title><title>Biopolymers</title><addtitle>Biopolymers</addtitle><description>ABSTRACT
Our recently discovered, selective, on‐resin route to N(τ)‐alkylated imidazolium‐containing histidine residues affords new strategies for peptide mimetic design. In this, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups serve as ring‐forming junctions. Interestingly, these cationic moieties subsequently serve to charge‐mask the phosphoamino acid group that directed their formation. Neighbor‐directed histidine N(τ)‐alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 104: 663–673, 2015.</description><subject>Alkylation</subject><subject>Biology</subject><subject>Biopolymers</subject><subject>Cationic</subject><subject>cationic dialkyl histidine</subject><subject>crystal structure</subject><subject>Crystallography, X-Ray</subject><subject>Formations</subject><subject>Histidine</subject><subject>Histidine - chemistry</subject><subject>Imidazoles - chemistry</subject><subject>Macrocyclic compounds</subject><subject>Macrocyclic Compounds - chemistry</subject><subject>peptide macrocycles</subject><subject>peptide macrocycles, phosphopeptides</subject><subject>Peptides</subject><subject>phosphopeptides</subject><subject>Phosphopeptides - chemistry</subject><subject>PLk1</subject><subject>polo kinase</subject><subject>polo-box domain</subject><subject>Residues</subject><subject>Strategy</subject><issn>0006-3525</issn><issn>1097-0282</issn><issn>1097-0282</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqNksFu1DAQhi0EokvhwAugiFN7SDu2E8fmUKlUsFRqF5BASL1YjuNszCZxsBNgOfN-vBIuaVdwQHAY-TDf_J759SP0GMMRBiDHpR2OCGGC30ELDKJIgXByFy0AgKU0J_keehDCR4Asoxjuoz3CcE44FAu0WRm7bkrn08p6o0dTJY0No61sb5JVcvDj-2Gq2s22VaN1_bPkNPFuGk0yusR2tlLfXGunLtWuH5Xtbb9OhsaFWIMZoopJOqW901vdmvAQ3atVG8yjm3cfvX_54t3Zq_Ti9fL87PQi1QwTnlackLqAvKSxNAeuDRNYKS4UrSnFmvKKCsqBlIxiU2mRY1HWFSihM8Eyuo9OZt1hKrvYN_3oVSsHbzvlt9IpK__s9LaRa_dZZpzlXNAo8HQWcNEJGbQdjW7iiX00SGJCOIYiQgc3v3j3aTJhlJ0N2rSt6o2bgsQ8-h0rx_9Gi4KxTAjG_wNlEFcs8PWZhzMaDQ7Bm3p3IQZ5nQsZcyF_5SKyT363ZEfeBiECxzPwxbZm-3cl-fz8za1kOk_EuJivuwnlN5IVtMjlh9VSLuHt1fLySshL-hMrD9Iz</recordid><startdate>201511</startdate><enddate>201511</enddate><creator>Qian, Wen-Jian</creator><creator>Park, Jung-Eun</creator><creator>Grant, Robert</creator><creator>Lai, Christopher C.</creator><creator>Kelley, James A.</creator><creator>Yaffe, Michael B.</creator><creator>Lee, Kyung S.</creator><creator>Burke Jr, Terrence R.</creator><general>Blackwell Publishing Ltd</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7U5</scope><scope>L7M</scope><scope>OTOTI</scope><scope>5PM</scope></search><sort><creationdate>201511</creationdate><title>Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles</title><author>Qian, Wen-Jian ; Park, Jung-Eun ; Grant, Robert ; Lai, Christopher C. ; Kelley, James A. ; Yaffe, Michael B. ; Lee, Kyung S. ; Burke Jr, Terrence R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6128-d822f705b305bc808ce691aa89a3f331c38d393802b631edc9519bfd0a9c49643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkylation</topic><topic>Biology</topic><topic>Biopolymers</topic><topic>Cationic</topic><topic>cationic dialkyl histidine</topic><topic>crystal structure</topic><topic>Crystallography, X-Ray</topic><topic>Formations</topic><topic>Histidine</topic><topic>Histidine - chemistry</topic><topic>Imidazoles - chemistry</topic><topic>Macrocyclic compounds</topic><topic>Macrocyclic Compounds - chemistry</topic><topic>peptide macrocycles</topic><topic>peptide macrocycles, phosphopeptides</topic><topic>Peptides</topic><topic>phosphopeptides</topic><topic>Phosphopeptides - chemistry</topic><topic>PLk1</topic><topic>polo kinase</topic><topic>polo-box domain</topic><topic>Residues</topic><topic>Strategy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qian, Wen-Jian</creatorcontrib><creatorcontrib>Park, Jung-Eun</creatorcontrib><creatorcontrib>Grant, Robert</creatorcontrib><creatorcontrib>Lai, Christopher C.</creatorcontrib><creatorcontrib>Kelley, James A.</creatorcontrib><creatorcontrib>Yaffe, Michael B.</creatorcontrib><creatorcontrib>Lee, Kyung S.</creatorcontrib><creatorcontrib>Burke Jr, Terrence R.</creatorcontrib><creatorcontrib>Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>OSTI.GOV</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Biopolymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Qian, Wen-Jian</au><au>Park, Jung-Eun</au><au>Grant, Robert</au><au>Lai, Christopher C.</au><au>Kelley, James A.</au><au>Yaffe, Michael B.</au><au>Lee, Kyung S.</au><au>Burke Jr, Terrence R.</au><aucorp>Argonne National Lab. 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Our recently discovered, selective, on‐resin route to N(τ)‐alkylated imidazolium‐containing histidine residues affords new strategies for peptide mimetic design. In this, we demonstrate the use of this chemistry to prepare a series of macrocyclic phosphopeptides, in which imidazolium groups serve as ring‐forming junctions. Interestingly, these cationic moieties subsequently serve to charge‐mask the phosphoamino acid group that directed their formation. Neighbor‐directed histidine N(τ)‐alkylation opens the door to new families of phosphopeptidomimetics for use in a range of chemical biology contexts. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 104: 663–673, 2015.</abstract><cop>United States</cop><pub>Blackwell Publishing Ltd</pub><pmid>26152807</pmid><doi>10.1002/bip.22698</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Biopolymers, 2015-11, Vol.104 (6), p.663-673 |
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| language | eng |
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| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Alkylation Biology Biopolymers Cationic cationic dialkyl histidine crystal structure Crystallography, X-Ray Formations Histidine Histidine - chemistry Imidazoles - chemistry Macrocyclic compounds Macrocyclic Compounds - chemistry peptide macrocycles peptide macrocycles, phosphopeptides Peptides phosphopeptides Phosphopeptides - chemistry PLk1 polo kinase polo-box domain Residues Strategy |
| title | Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles |
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