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Peucemycin is a
polyketide
In organic chemistry, polyketides are a class of natural products derived from a Precursor (chemistry), precursor molecule consisting of a Polymer backbone, chain of alternating ketone (, or Carbonyl reduction, its reduced forms) and Methylene gro ...
produced by ''Streptomyces peucetius
''Streptomyces peucetius'' is a bacterium species in the genus ''Streptomyces''.
''S. peucetius'' produces the anthracycline antitumor antibiotics daunorubicin and doxorubicin
Doxorubicin, sold under the brand name Adriamycin among others ...
'', a Gram-positive
In bacteriology, gram-positive bacteria are bacteria that give a positive result in the Gram stain test, which is traditionally used to quickly classify bacteria into two broad categories according to their type of cell wall.
The Gram stain is ...
filamentous bacteria that also produces the anticancer compounds daunorubicin
Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically it is used for acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. I ...
and doxorubicin
Doxorubicin, sold under the brand name Adriamycin among others, is a chemotherapy medication used to treat cancer. This includes breast cancer, bladder cancer, Kaposi's sarcoma, lymphoma, and acute lymphocytic leukemia. It is often used toge ...
. This compound was elucidated from a cryptic biosynthetic gene cluster and is produced under temperature-specific conditions for bacterial growth (metabolite is present at 18 °C but not 28 °C). Peucemycin has demonstrated bioactivity against growth of '' S. aureus'', '' P. hauseri'', and ''S. enterica
S is the nineteenth letter of the English alphabet.
S may also refer to:
History
* an Anglo-Saxon charter's number in Peter Sawyer's, catalogue
Language and linguistics
* Long s (ſ), a form of the lower-case letter s formerly used where "s ...
'' and also is weakly active against cancer cell lines. Peucemycin is biosynthesized through a Type 1 PKS system.
Biosynthesis
Peucemycin is synthesized through a type 1 polyketide synthase with 8 proposed modules from 5 PKS-related genes (''peuA-peuE).'' The type 1 PKS pathway used for biosynthesis is shown in Figure 1. The first gene, ''peuA,'' encodes for an initiation module and two elongation modules. The structure of the ketosynthase enzyme in the initiation module has a mutation of a cysteine residue to a glutamine residue that allows for decarboxylation of the starting material without condensation. The next gene, ''peuB,'' encodes for modules 3 and 4. Sequencing data of Module 4 indicates presence of a dehydratase enzyme, but amino acid mutations leave this enzyme inactivated, meaning a singular hydroxyl group at carbon 9 is generated. Module 5 is encoded by ''peuC'', and an additional gene, ''peuI'', is proposed to introduce the butyl malonyl-CoA in this module. Modules 6 and 7 are encoded by ''peuD'' and ''peuE'' respectively. The forming polyketide chain is hydroxylated with cytochrome P450 enzymes, ''peuH'' and ''peuG,'' and the terminal thioesterase domain in Module 7 catalyzes the product release and macrocycle formation to form peucemycin.
References
Polyketides Lactones Heterocyclic compounds with 2 rings Twelve-membered rings Secondary alcohols {{Bacteria-stub