What question did this study set out to answer?

To isolate and resolve the molecular planar structures and absolute stereochemistry of TMC-95A–D, four novel proteasome inhibitors derived from the fungus Apiospora montagnei.

February 1, 2000The Journal of Organic Chemistry

Structures of TMC-95A−D: Novel Proteasome Inhibitors from Apiospora montagnei Sacc. TC 1093

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Authors

JKJun KohnoYokogawa Electric (Japan)YKYutaka KoguchiKawasaki Medical School MNMAKI NISHIOJapanese Foundation For Cancer Research

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Implication

Natural product isolation study uncovers novel cyclic peptide proteasome inhibitors TMC-95A–D from Apiospora montagnei, highlighting new scaffolds for enzyme inhibition.

Key Points

To isolate and resolve the molecular planar structures and absolute stereochemistry of TMC-95A–D, four novel proteasome inhibitors derived from the fungus Apiospora montagnei.
Purified TMC-95A–D from the fermentation broth of Apiospora montagnei Sacc. TC 1093 and established their molecular formulas using high-resolution FAB-MS.
Elucidated planar structures through 1D and 2D NMR spectroscopy combined with chemical degradation reactions.
Determined absolute stereochemistry via chiral TLC and HPLC analyses of degradation fragments, together with ROESY correlation spectra and 1H-1H coupling constants.
Established the identical molecular formula C33H38N6O10 across compounds 1–4, identifying each as a modified cyclic peptide containing L-tyrosine, L-asparagine, oxidized L-tryptophan, (Z)-1-propenylamine, and 3-methyl-2-oxopentanoic acid.
Determined the absolute configurations across stereocenters C-6, C-7, C-8, C-11, C-14, and C-36, establishing that TMC-95A–D are diastereomers at positions C-7 and C-36.

Cite This Study

Kohno et al. (2000) studied this question.

synapsesocial.com/papers/6a00a196b124fe581985f932 https://doi.org/10.1021/jo991375+

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Implication

Natural product isolation study uncovers novel cyclic peptide proteasome inhibitors TMC-95A–D from Apiospora montagnei, highlighting new scaffolds for enzyme inhibition.

Structures of TMC-95A−D: Novel Proteasome Inhibitors from Apiospora montagnei Sacc. TC 1093

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Cite This Study

Structures of TMC-95A−D: Novel Proteasome Inhibitors from Apiospora montagnei Sacc. TC 1093

Discussion

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Implication

Key Points

Cite This Study

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