A lipopeptide biosurfactant
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Orfamide A

Item No. 28131

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(3-hydroxy-1-oxotetradecyl)-L-leucyl-D-α-glutamyl-D-allothreonyl-D-alloisoleucyl-L-leucyl-D-seryl-L-leucyl-L-leucyl-D-seryl-L-valine, (10→3)-lactone
CAS Number
939960-34-6
Molecular Formula
C64H114N10O17
Formula Weight
1295.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
CC(C)C[C@@H](C(N[C@@H](CC(C)C)C(N[C@@](CO)([H])C(N[C@@H](C(C)C)C(O[C@H](C)[C@H]1NC([C@H](NC([C@H](CC(C)C)NC(CC(O)CCCCCCCCCCC)=O)=O)CCC(O)=O)=O)=O)=O)=O)=O)NC([C@@H](CO)NC([C@@](CC(C)C)([H])NC([C@]([C@H](CC)C)([H])NC1=O)=O)=O)=O
InChi Code
InChI=1S/C64H114N10O17/c1-15-17-18-19-20-21-22-23-24-25-42(77)32-50(78)65-44(28-35(3)4)56(82)66-43(26-27-51(79)80)55(81)74-54-41(14)91-64(90)52(39(11)12)72-61(87)49(34-76)71-58(84)46(30-37(7)8)67-57(83)45(29-36(5)6)68-60(86)48(33-75)70-59(85)47(31-38(9)10)69-62(88)53(40(13)16-2)73-63(54)89/h35-49,52-54,75-77H,15-34H2,1-14H3,(H,65,78)(H,66,82)(H,67,83)(H,68,86)(H,69,88)(H,70,85)(H,71,84)(H,72,87)(H,73,89)(H,74,81)(H,79,80)/t40-,41+,42?,43+,44-,45-,46-,47-,48+,49+,52-,53+,54+/m0/s1
InChi Key
AFOLBAYDTRBYBA-AAYKRXRBSA-N
Origin
Bacterium/Pseudomonas fluorescens
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Orfamide A is a lipopeptide biosurfactant originally isolated from P. protegens.1,2,3 It induces mortality in adult green peach aphids (LC50 = 34.5 μg/ml).1 Orfamide A (50 μM) blocks appressoria formation in M. oryzae isolates and reduces the number of sporulating blast lesions in M. oryzae-infected plants.2 It is also active against T. b. brucei (IC50 = 6 µM).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jang, J.Y., Yang, S.Y., Kim, Y.C., et al. Identification of orfamide A as an insecticidal metabolite produced by Pseudomonas protegens F6. J. Agric. Food Chem. 61(28), 6786-6791 (2013).

    2. Ma, Z., Geudens, N., Kieu, N.P., et al. Biosynthesis, chemical structure, and structure-activity relationship of orfamide lipopeptides produced by Pseudomonas protegens and related species. Front. Microbiol. 7, 382 (2016).

    3. Gross, H., Stockwell, V.O., Henkels, M.D., et al. The genomisotopic approach: A systematic method to isolate products of orphan biosynthetic gene clusters. Chem. Biol. 14(1), 53-63 (2007).