The stereoselective construction of E- and Z-Delta-Ile from E-dehydroamino acid ester: the synthesis of the phomopsin A tripeptide side chain
The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy) carbonyl)amino)-2-(diphenoxyphosphoryl) acetate as a common synthetic precursor for the synthesis of E-Delta-dehydroisoleucine and E-Delta-aspartate.
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Published in | Chemical communications (Cambridge, England) Vol. 52; no. 7; pp. 1478 - 1481 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
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Royal Soc Chemistry
25.01.2016
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Abstract | The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy) carbonyl)amino)-2-(diphenoxyphosphoryl) acetate as a common synthetic precursor for the synthesis of E-Delta-dehydroisoleucine and E-Delta-aspartate. |
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AbstractList | The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy)carbonyl)amino)-2-(diphenoxyphosphoryl)acetate as a common synthetic precursor for the synthesis of
E
-Δ-dehydroisoleucine and
E
-Δ-aspartate. The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy)carbonyl)amino)-2-(diphenoxyphosphoryl)acetate as a common synthetic precursor for the synthesis of E-Δ-dehydroisoleucine and E-Δ-aspartate. The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy) carbonyl)amino)-2-(diphenoxyphosphoryl) acetate as a common synthetic precursor for the synthesis of E-Delta-dehydroisoleucine and E-Delta-aspartate. |
Author | Shinada, Tetsuro Yasukawa, Yoshifumi Nishimura, Akito Karita, Yuma Yasuno, Yoko Ohfune, Yasufumi |
Author_xml | – sequence: 1 givenname: Yoko surname: Yasuno fullname: Yasuno, Yoko organization: Osaka City Univ, Grad Sch Sci, Osaka 5588585, Japan – sequence: 2 givenname: Akito surname: Nishimura fullname: Nishimura, Akito organization: Osaka City Univ, Grad Sch Sci, Osaka 5588585, Japan – sequence: 3 givenname: Yoshifumi surname: Yasukawa fullname: Yasukawa, Yoshifumi organization: Osaka City Univ, Grad Sch Sci, Osaka 5588585, Japan – sequence: 4 givenname: Yuma surname: Karita fullname: Karita, Yuma organization: Osaka City Univ, Grad Sch Sci, Osaka 5588585, Japan – sequence: 5 givenname: Yasufumi surname: Ohfune fullname: Ohfune, Yasufumi organization: Osaka City Univ, Grad Sch Sci, Osaka 5588585, Japan – sequence: 6 givenname: Tetsuro surname: Shinada fullname: Shinada, Tetsuro organization: Osaka City Univ, Grad Sch Sci, Osaka 5588585, Japan |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26658962$$D View this record in MEDLINE/PubMed |
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CitedBy_id | crossref_primary_10_1002_ange_201916517 crossref_primary_10_1002_ange_202002328 crossref_primary_10_1002_anie_202002328 crossref_primary_10_1002_anie_201916517 crossref_primary_10_1016_j_tet_2017_03_060 crossref_primary_10_1002_chem_202003858 crossref_primary_10_1039_D1CC01277K crossref_primary_10_5059_yukigoseikyokaishi_80_331 crossref_primary_10_1002_ajoc_202300227 crossref_primary_10_1039_D2QO00050D |
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Keywords | ELUCIDATION CHEMICAL BIOLOGY PEPTIDES AMINO-ACIDS NATURAL-PRODUCTS CONFIGURATION LEPTOSTROMIFORMIS IDENTIFICATION DERIVATIVES |
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Snippet | The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy) carbonyl)amino)-2-(diphenoxyphosphoryl)... The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl... |
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SubjectTerms | Amino Acids - chemistry Chemistry Chemistry, Multidisciplinary Esters - chemistry Mycotoxins - chemical synthesis Mycotoxins - chemistry Oligopeptides - chemical synthesis Physical Sciences Proton Magnetic Resonance Spectroscopy Science & Technology |
Title | The stereoselective construction of E- and Z-Delta-Ile from E-dehydroamino acid ester: the synthesis of the phomopsin A tripeptide side chain |
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