Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water.

2.50
Hdl Handle:
http://hdl.handle.net/10033/621215
Title:
Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water.
Authors:
Corr, M J; Sharma, S V; Pubill-Ulldemolins, C; Bown, R T; Poirot, P; Smith, D R M; Cartmell, C; Abou Fayad, A; Goss, R J M
Abstract:
The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite.
Affiliation:
Hel,holtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr.7, 38124 Braunschweig, Germany.
Citation:
Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water. 2017, 8 (3):2039-2046 Chem Sci
Journal:
Chemical science
Issue Date:
1-Mar-2017
URI:
http://hdl.handle.net/10033/621215
DOI:
10.1039/c6sc04423a
PubMed ID:
28451322
Type:
Article
Language:
en
ISSN:
2041-6520
Appears in Collections:
publications of the department of microbial natural substances ([HIPS]MINS)

Full metadata record

DC FieldValue Language
dc.contributor.authorCorr, M Jen
dc.contributor.authorSharma, S Ven
dc.contributor.authorPubill-Ulldemolins, Cen
dc.contributor.authorBown, R Ten
dc.contributor.authorPoirot, Pen
dc.contributor.authorSmith, D R Men
dc.contributor.authorCartmell, Cen
dc.contributor.authorAbou Fayad, Aen
dc.contributor.authorGoss, R J Men
dc.date.accessioned2018-01-02T09:25:10Z-
dc.date.available2018-01-02T09:25:10Z-
dc.date.issued2017-03-01-
dc.identifier.citationSonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water. 2017, 8 (3):2039-2046 Chem Scien
dc.identifier.issn2041-6520-
dc.identifier.pmid28451322-
dc.identifier.doi10.1039/c6sc04423a-
dc.identifier.urihttp://hdl.handle.net/10033/621215-
dc.description.abstractThe blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite.en
dc.language.isoenen
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/614779en
dc.rightsopenAccessen
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.titleSonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water.en
dc.typeArticleen
dc.contributor.departmentHel,holtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr.7, 38124 Braunschweig, Germany.en
dc.identifier.journalChemical scienceen

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