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Crisamicin A (1 in Figure 1), a natural product that contains
two pyran-fused lactones that are C2-symmetric to each other,
represents a prominent member of the dimeric pyranonaphthoquinone
family of antibiotics (2-51 in Figure 1) and was
first isolated in 1986 from the micro-organism Micromonospora
purpureochromogenes that was obtained from a mud
sample in the Philippines.2 Crisamicin A exhibited activity
against B16 murine melanoma cells, the herpes simplex, and
vesicular stomatitis viruses.3 A more recent investigation also
uncovered important cytotoxic and antimicrobial activities
of its close structural analogues; for example, a new
pyranonaphthoquinone antibiotic termed GTRI-BB produced
by Micromonospora sp. SA-246, which is structurally
directly derived from crisamicin A through ring opening of
one of its two lactone rings, was found to be a stronger
inhibitor on the growth of tumor cell lines than the common
anticancer compound adriamycin
While the syntheses of several monomeric antibiotics have
been reported, the total synthesis of such a dimeric pyranonaphthoquinone
as crisamicin A has yet to be achieved.5
Conceivably, these dimeric structures could be constructed
by homocoupling of their monomeric precursors, a particular
challenge that has defeated all the attempts so far6 but, if
realized generally, should have greater implication in rapidly
assembling these structures.
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