Prolinimines: N-Amino-l-Pro-methyl Ester (Hydrazine) Schiff Bases from a Fish Gastrointestinal Tract-Derived Fungus, Trichoderma sp. CMB-F563

Mohamed, Osama G, Khalil, Zeinab G and Capon, Robert J (2018) Prolinimines: N-Amino-l-Pro-methyl Ester (Hydrazine) Schiff Bases from a Fish Gastrointestinal Tract-Derived Fungus, Trichoderma sp. CMB-F563. Organic letters, . doi:10.1021/acs.orglett.7b03666


Author Mohamed, Osama G
Khalil, Zeinab G
Capon, Robert J
Title Prolinimines: N-Amino-l-Pro-methyl Ester (Hydrazine) Schiff Bases from a Fish Gastrointestinal Tract-Derived Fungus, Trichoderma sp. CMB-F563
Journal name Organic letters   Check publisher's open access policy
ISSN 1523-7052
Publication date 2018-01-09
Sub-type Article (original research)
DOI 10.1021/acs.orglett.7b03666
Open Access Status Not yet assessed
Abstract A rice cultivation of a fish gastrointestinal tract-derived fungus, Trichoderma sp. CMB-F563, yielded natural products incorporating a rare hydrazine moiety, embedded within a Schiff base. Structures inclusive of absolute configurations were assigned to prolinimines A-D (1-4) on the basis of detailed spectroscopic and C3 Marfey's analysis, as well as biosynthetic considerations, biomimetic total synthesis, and chemical transformations. Of note, monomeric 1 proved to be acid labile and, during isolation, underwent quantitative transformation to dimeric 3 and trimeric 4. Prolinimines are only the second reported natural products incorporating an N-amino-Pro residue, the first to include l-Pro, the first to occur as Schiff bases, and the first to be isolated from a microorganism.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Pubmed Import
 
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Created: Wed, 10 Jan 2018, 20:37:32 EST