Cyclo(L-Ser-L-Ser)
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Cyclo(L-Ser-L-Ser)

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Category
Others
Catalog number
BAT-004981
CAS number
23409-30-5
Molecular Formula
C6H10N2O4
Molecular Weight
174.16
Cyclo(L-Ser-L-Ser)
IUPAC Name
(3S,6S)-3,6-bis(hydroxymethyl)piperazine-2,5-dione
Synonyms
Cyclo(-Ser-Ser)
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.353±0.06 g/cm3(Predicted)
Melting Point
241-245 °C
Boiling Point
675.0±40.0 °C(Predicted)
Storage
Store at -20 °C
InChI
InChI=1S/C6H10N2O4/c9-1-3-5(11)8-4(2-10)6(12)7-3/h3-4,9-10H,1-2H2,(H,7,12)(H,8,11)/t3-,4-/m0/s1
InChI Key
SUWGHSHLNOADHI-IMJSIDKUSA-N
Canonical SMILES
C(C1C(=O)NC(C(=O)N1)CO)O
1.RsmA regulates Aspergillus fumigatus gliotoxin cluster metabolites including cyclo(L-Phe-L-Ser), a potential new diagnostic marker for invasive aspergillosis.
Sekonyela R1, Palmer JM, Bok JW, Jain S, Berthier E, Forseth R, Schroeder F, Keller NP. PLoS One. 2013 May 6;8(5):e62591. doi: 10.1371/journal.pone.0062591. Print 2013.
Dimeric basic leucine zipper (bZIP) proteins are conserved transcriptional enhancers found in all eukaryotes. A recently reported and novel function for bZIPs is association of these proteins with secondary metabolite production in filamentous fungi. In particular a Yap-like bZIP termed RsmA (restorer of secondary metabolism A) was identified in Aspergillus nidulans that positively regulates the carcinogen sterigmatocystin. To assess for conserved function for RsmA, we examined a role of this protein in secondary metabolism in the pathogen A. fumigatus. RsmA was found to positively regulate gliotoxin where overexpression (OE) of rsmA led to 2-100 fold increases of twelve gli cluster metabolites in culture medium including the newly identified gli metabolite cyclo(L-Phe-L-Ser). Lungs from both wild type and OErsmA infected mice contained gliotoxin (2.3 fold higher in OErsmA treatment) as well as the gliotoxin precursor cyclo(L-Phe-L-Ser) (3.
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