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Synthesis of eight stereoisomers of pochonicine: nanomolar inhibition of β-N-acetylhexosaminidases.

Abstract:

Pochonicine, the first naturally occurring polyhydroxylated pyrrolizidine containing an acetamidomethyl group, which was isolated from Pochonia suchlasporia var. suchlasporia TAMA 87, together with its enantiomer and their C-1 and/or C-3 epimers, have been synthesized from the sugar-derived cyclic nitrones 9D and 9L, respectively. An in-depth NMR study showed that both the (1)H and (13)C NMR spectra of the synthetic pochonicines (1D and 1L) matched very well with those of natural pochonicine ...

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Publication status:
Published

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Publisher copy:
10.1021/jo401694e

Authors


Nakagawa, S More by this author
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Journal:
The Journal of organic chemistry
Volume:
78
Issue:
20
Pages:
10298-10309
Publication date:
2013-10-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:53a5b2ec-7660-45a5-b75d-87529bfd8acf
Source identifiers:
439397
Local pid:
pubs:439397

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