Synthesis of N-Fmoc-O- (N‘-Boc-N‘-methyl)-aminohomoserine, an Amino Acid for the Facile Preparation of Neoglycopeptides
The synthesis of N-Fmoc-O-(N‘-Boc-N‘-methyl)-aminohomoserine in 35% overall yield from l-homoserine is described. This amino acid can be efficiently incorporated into peptides using Fmoc-chemistry-based solid-phase peptide synthesis, and the resulting peptides can be chemoselectively glycosylated at...
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| Veröffentlicht in: | Journal of organic chemistry 2003-01, Vol.68 (1), p.195-197 |
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| container_end_page | 197 |
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| container_issue | 1 |
| container_start_page | 195 |
| container_title | Journal of organic chemistry |
| container_volume | 68 |
| creator | Carrasco, Michael R Brown, Ryan T Serafimova, Iana M Silva, Oscar |
| description | The synthesis of N-Fmoc-O-(N‘-Boc-N‘-methyl)-aminohomoserine in 35% overall yield from l-homoserine is described. This amino acid can be efficiently incorporated into peptides using Fmoc-chemistry-based solid-phase peptide synthesis, and the resulting peptides can be chemoselectively glycosylated at the aminooxy side chains to generate neoglycopeptides. The synthesis of this derivative greatly expands the availability of a previously developed neoglycopeptide synthesis strategy. |
| doi_str_mv | 10.1021/jo026641p |
| format | Article |
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This amino acid can be efficiently incorporated into peptides using Fmoc-chemistry-based solid-phase peptide synthesis, and the resulting peptides can be chemoselectively glycosylated at the aminooxy side chains to generate neoglycopeptides. The synthesis of this derivative greatly expands the availability of a previously developed neoglycopeptide synthesis strategy.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo026641p</identifier><identifier>PMID: 12515483</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aliphatic compounds ; Chemistry ; Exact sciences and technology ; Glycoproteins - chemical synthesis ; Homoserine - analogs & derivatives ; Homoserine - analysis ; Homoserine - chemical synthesis ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Organic chemistry ; Peptides - chemical synthesis ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2003-01, Vol.68 (1), p.195-197</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-df65e0c7239d61143cc9028b58f3525c9bd77e98e4368f3db37e40f423a13393</citedby><cites>FETCH-LOGICAL-a379t-df65e0c7239d61143cc9028b58f3525c9bd77e98e4368f3db37e40f423a13393</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/jo026641p$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo026641p$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14458825$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12515483$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Carrasco, Michael R</creatorcontrib><creatorcontrib>Brown, Ryan T</creatorcontrib><creatorcontrib>Serafimova, Iana M</creatorcontrib><creatorcontrib>Silva, Oscar</creatorcontrib><title>Synthesis of N-Fmoc-O- (N‘-Boc-N‘-methyl)-aminohomoserine, an Amino Acid for the Facile Preparation of Neoglycopeptides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The synthesis of N-Fmoc-O-(N‘-Boc-N‘-methyl)-aminohomoserine in 35% overall yield from l-homoserine is described. This amino acid can be efficiently incorporated into peptides using Fmoc-chemistry-based solid-phase peptide synthesis, and the resulting peptides can be chemoselectively glycosylated at the aminooxy side chains to generate neoglycopeptides. The synthesis of this derivative greatly expands the availability of a previously developed neoglycopeptide synthesis strategy.</description><subject>Aliphatic compounds</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Glycoproteins - chemical synthesis</subject><subject>Homoserine - analogs & derivatives</subject><subject>Homoserine - analysis</subject><subject>Homoserine - chemical synthesis</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Peptides - chemical synthesis</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM9uEzEQhy1ERUPhwAsgX0BUwuD_u3sMbUORQlupOXGxHO8scdldb-2N1IgLj9Hn40lwm6i54Mt4Zj59Gv0QesPoJ0Y5-3wTKNdasuEZmjDFKdEVlc_RhFLOieBaHKKXKd3Q_JRSL9Ah44opWYoJ-n296ccVJJ9waPAFmXXBkUuCP1z8_XNPvuTm8dPBuNq0x8R2vg-r0IUE0ffwEdseTx9meOp8jZsQcbbhmXW-BXwVYbDRjj70j3YIP9uNCwMMo68hvUIHjW0TvN7VI7SYnS1Ozsn88uu3k-mcWFFUI6kbrYC6gouq1oxJ4VxFeblUZSMUV65a1kUBVQlS6Dyql6IASRvJhWVCVOIIvd9qhxhu15BG0_nkoG1tD2GdTMErpVUpMni8BV0MKUVozBB9Z-PGMGoegjZPQWf27U66XnZQ78ldshl4twNscrZtou2dT3tOSlWWXGWObDmfRrh72tv4y-hCFMosrq7NXJ9q_n1OzY-917qU71nHPkf3nwP_AUvBoRA</recordid><startdate>20030110</startdate><enddate>20030110</enddate><creator>Carrasco, Michael R</creator><creator>Brown, Ryan T</creator><creator>Serafimova, Iana M</creator><creator>Silva, Oscar</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</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>20030110</creationdate><title>Synthesis of N-Fmoc-O- (N‘-Boc-N‘-methyl)-aminohomoserine, an Amino Acid for the Facile Preparation of Neoglycopeptides</title><author>Carrasco, Michael R ; Brown, Ryan T ; Serafimova, Iana M ; Silva, Oscar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-df65e0c7239d61143cc9028b58f3525c9bd77e98e4368f3db37e40f423a13393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Aliphatic compounds</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Glycoproteins - chemical synthesis</topic><topic>Homoserine - analogs & derivatives</topic><topic>Homoserine - analysis</topic><topic>Homoserine - chemical synthesis</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Peptides - chemical synthesis</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Carrasco, Michael R</creatorcontrib><creatorcontrib>Brown, Ryan T</creatorcontrib><creatorcontrib>Serafimova, Iana M</creatorcontrib><creatorcontrib>Silva, Oscar</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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 organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Carrasco, Michael R</au><au>Brown, Ryan T</au><au>Serafimova, Iana M</au><au>Silva, Oscar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of N-Fmoc-O- (N‘-Boc-N‘-methyl)-aminohomoserine, an Amino Acid for the Facile Preparation of Neoglycopeptides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-01-10</date><risdate>2003</risdate><volume>68</volume><issue>1</issue><spage>195</spage><epage>197</epage><pages>195-197</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The synthesis of N-Fmoc-O-(N‘-Boc-N‘-methyl)-aminohomoserine in 35% overall yield from l-homoserine is described. This amino acid can be efficiently incorporated into peptides using Fmoc-chemistry-based solid-phase peptide synthesis, and the resulting peptides can be chemoselectively glycosylated at the aminooxy side chains to generate neoglycopeptides. The synthesis of this derivative greatly expands the availability of a previously developed neoglycopeptide synthesis strategy.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12515483</pmid><doi>10.1021/jo026641p</doi><tpages>3</tpages></addata></record> |
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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2003-01, Vol.68 (1), p.195-197 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Aliphatic compounds Chemistry Exact sciences and technology Glycoproteins - chemical synthesis Homoserine - analogs & derivatives Homoserine - analysis Homoserine - chemical synthesis Magnetic Resonance Spectroscopy Molecular Structure Organic chemistry Peptides - chemical synthesis Preparations and properties |
| title | Synthesis of N-Fmoc-O- (N‘-Boc-N‘-methyl)-aminohomoserine, an Amino Acid for the Facile Preparation of Neoglycopeptides |
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