The Revised Structure of the Cyclic Octapeptide Surugamide A
Surugamides are a group of non-ribosomal peptides isolated from marine-derived Streptomyces. Surugamide A (1) and its closely related derivatives, surugamides B–E (2–5), are D-amino acid containing cyclic octapeptides with cathepsin B inhibitory activity. The D-isoleucine (Ile), the nonproteinogenic...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2019/05/01, Vol.67(5), pp.476-480 |
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| creator | Matsuda, Kenichi Kuranaga, Takefumi Sano, Ayae Ninomiya, Akihiro Takada, Kentaro Wakimoto, Toshiyuki |
| description | Surugamides are a group of non-ribosomal peptides isolated from marine-derived Streptomyces. Surugamide A (1) and its closely related derivatives, surugamides B–E (2–5), are D-amino acid containing cyclic octapeptides with cathepsin B inhibitory activity. The D-isoleucine (Ile), the nonproteinogenic amino acid residue embedded in 1, is less common in natural peptides because a rare Cβ-epimerization is required for its biosynthesis. Taking advantage of the synthetic route of 2 previously established by our group, we synthesized the cyclic octapeptide 1 containing D-Ile by solid phase peptide synthesis. The structure of 1 actually contains D-allo-Ile in place of D-Ile, which was corroborated by chemical syntheses and chromatographic comparisons. |
| doi_str_mv | 10.1248/cpb.c19-00002 |
| format | Article |
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Surugamide A (1) and its closely related derivatives, surugamides B–E (2–5), are D-amino acid containing cyclic octapeptides with cathepsin B inhibitory activity. The D-isoleucine (Ile), the nonproteinogenic amino acid residue embedded in 1, is less common in natural peptides because a rare Cβ-epimerization is required for its biosynthesis. Taking advantage of the synthetic route of 2 previously established by our group, we synthesized the cyclic octapeptide 1 containing D-Ile by solid phase peptide synthesis. The structure of 1 actually contains D-allo-Ile in place of D-Ile, which was corroborated by chemical syntheses and chromatographic comparisons.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c19-00002</identifier><identifier>PMID: 31061373</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Amino Acid Sequence ; Amino acids ; Biosynthesis ; Cathepsin B ; D-amino acid ; Isoleucine ; Isoleucine - chemical synthesis ; Isoleucine - chemistry ; marine natural product ; non-ribosomal peptide ; Octapeptides ; Organic chemistry ; Peptide synthesis ; Peptides ; Peptides, Cyclic - chemical synthesis ; Peptides, Cyclic - chemistry ; Protein Conformation ; Solid phases ; Solid-Phase Synthesis Techniques ; Stereoisomerism ; Streptomyces - chemistry ; structural revision</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2019/05/01, Vol.67(5), pp.476-480</ispartof><rights>2019 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c585t-805467456d326ad7116804171fa038c60a98d8f67d1fd31bcdda1ac01e6e36153</citedby><cites>FETCH-LOGICAL-c585t-805467456d326ad7116804171fa038c60a98d8f67d1fd31bcdda1ac01e6e36153</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1882,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31061373$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Matsuda, Kenichi</creatorcontrib><creatorcontrib>Kuranaga, Takefumi</creatorcontrib><creatorcontrib>Sano, Ayae</creatorcontrib><creatorcontrib>Ninomiya, Akihiro</creatorcontrib><creatorcontrib>Takada, Kentaro</creatorcontrib><creatorcontrib>Wakimoto, Toshiyuki</creatorcontrib><creatorcontrib>bGraduate School of Agricultural and Sciences</creatorcontrib><creatorcontrib>The University of Tokyo</creatorcontrib><creatorcontrib>aFaculty of Pharmaceutical Sciences</creatorcontrib><creatorcontrib>Hokkaido University</creatorcontrib><title>The Revised Structure of the Cyclic Octapeptide Surugamide A</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Surugamides are a group of non-ribosomal peptides isolated from marine-derived Streptomyces. Surugamide A (1) and its closely related derivatives, surugamides B–E (2–5), are D-amino acid containing cyclic octapeptides with cathepsin B inhibitory activity. The D-isoleucine (Ile), the nonproteinogenic amino acid residue embedded in 1, is less common in natural peptides because a rare Cβ-epimerization is required for its biosynthesis. Taking advantage of the synthetic route of 2 previously established by our group, we synthesized the cyclic octapeptide 1 containing D-Ile by solid phase peptide synthesis. The structure of 1 actually contains D-allo-Ile in place of D-Ile, which was corroborated by chemical syntheses and chromatographic comparisons.</description><subject>Amino Acid Sequence</subject><subject>Amino acids</subject><subject>Biosynthesis</subject><subject>Cathepsin B</subject><subject>D-amino acid</subject><subject>Isoleucine</subject><subject>Isoleucine - chemical synthesis</subject><subject>Isoleucine - chemistry</subject><subject>marine natural product</subject><subject>non-ribosomal peptide</subject><subject>Octapeptides</subject><subject>Organic chemistry</subject><subject>Peptide synthesis</subject><subject>Peptides</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Protein Conformation</subject><subject>Solid phases</subject><subject>Solid-Phase Synthesis Techniques</subject><subject>Stereoisomerism</subject><subject>Streptomyces - chemistry</subject><subject>structural revision</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkM1rGzEQxUVpaZy0x17LQi-9bKqRVh-GXoJp0kIg0KRnIUuzscx-VdIW8t9Xa6cOVIfRoPnx5ukR8gHoJbBGf3HT9tLBuqblsFdkBbxRtWCMvyar8rSuGZf8jJyntC-AoIq_JWccqASu-Ip8fdhh9RP_hIS-us9xdnmOWI1tlctg8-S64Ko7l-2EUw4eq_s5zo-2X9qrd-RNa7uE75_vC_Lr-tvD5nt9e3fzY3N1WzuhRa41FY1UjZCeM2m9ApCaNqCgtZRrJ6lda69bqTy0nsPWeW_BOgookUsQ_IJ8PupOcfw9Y8qmD8lh19kBxzmZ8lsGCwkF_fQfuh_nOBR3CwW62ICFqo-Ui2NKEVszxdDb-GSAmiVWU2I1JVZziLXwH59V522P_kT_y7EAN0egTIOz3Th0YcCX3S4pt8M-GEYPolJRYSgwQxslS9GUs2JtLYvS5qi0T9k-4mmVjTm4Dg_GpDJiKSeDL9OdjQYH_hcL7J5Y</recordid><startdate>20190501</startdate><enddate>20190501</enddate><creator>Matsuda, Kenichi</creator><creator>Kuranaga, Takefumi</creator><creator>Sano, Ayae</creator><creator>Ninomiya, Akihiro</creator><creator>Takada, Kentaro</creator><creator>Wakimoto, Toshiyuki</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20190501</creationdate><title>The Revised Structure of the Cyclic Octapeptide Surugamide A</title><author>Matsuda, Kenichi ; Kuranaga, Takefumi ; Sano, Ayae ; Ninomiya, Akihiro ; Takada, Kentaro ; Wakimoto, Toshiyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c585t-805467456d326ad7116804171fa038c60a98d8f67d1fd31bcdda1ac01e6e36153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Amino Acid Sequence</topic><topic>Amino acids</topic><topic>Biosynthesis</topic><topic>Cathepsin B</topic><topic>D-amino acid</topic><topic>Isoleucine</topic><topic>Isoleucine - chemical synthesis</topic><topic>Isoleucine - chemistry</topic><topic>marine natural product</topic><topic>non-ribosomal peptide</topic><topic>Octapeptides</topic><topic>Organic chemistry</topic><topic>Peptide synthesis</topic><topic>Peptides</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Protein Conformation</topic><topic>Solid phases</topic><topic>Solid-Phase Synthesis Techniques</topic><topic>Stereoisomerism</topic><topic>Streptomyces - chemistry</topic><topic>structural revision</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matsuda, Kenichi</creatorcontrib><creatorcontrib>Kuranaga, Takefumi</creatorcontrib><creatorcontrib>Sano, Ayae</creatorcontrib><creatorcontrib>Ninomiya, Akihiro</creatorcontrib><creatorcontrib>Takada, Kentaro</creatorcontrib><creatorcontrib>Wakimoto, Toshiyuki</creatorcontrib><creatorcontrib>bGraduate School of Agricultural and Sciences</creatorcontrib><creatorcontrib>The University of Tokyo</creatorcontrib><creatorcontrib>aFaculty of Pharmaceutical Sciences</creatorcontrib><creatorcontrib>Hokkaido University</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matsuda, Kenichi</au><au>Kuranaga, Takefumi</au><au>Sano, Ayae</au><au>Ninomiya, Akihiro</au><au>Takada, Kentaro</au><au>Wakimoto, Toshiyuki</au><aucorp>bGraduate School of Agricultural and Sciences</aucorp><aucorp>The University of Tokyo</aucorp><aucorp>aFaculty of Pharmaceutical Sciences</aucorp><aucorp>Hokkaido University</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Revised Structure of the Cyclic Octapeptide Surugamide A</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. 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| source | MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Amino Acid Sequence Amino acids Biosynthesis Cathepsin B D-amino acid Isoleucine Isoleucine - chemical synthesis Isoleucine - chemistry marine natural product non-ribosomal peptide Octapeptides Organic chemistry Peptide synthesis Peptides Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Protein Conformation Solid phases Solid-Phase Synthesis Techniques Stereoisomerism Streptomyces - chemistry structural revision |
| title | The Revised Structure of the Cyclic Octapeptide Surugamide A |
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