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M5280

Sigma-Aldrich

Mastoparan, Vespula lewisii

≥97% (HPLC), powder

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About This Item

Empirical Formula (Hill Notation):
C70H131N19O15
CAS Number:
72093-21-1
Molecular Weight:
1478.91
Beilstein:
5491949
MDL number:
MFCD00076865
UNSPSC Code:
41106300
PubChem Substance ID:
329818006
NACRES:
NA.32

biological source

synthetic

Quality Level

200

Assay

≥97% (HPLC)

form

powder

color

white

storage temp.

−20°C

SMILES string

CC[C@H](C)[C@H](N)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)NC([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(N)=O

InChI

1S/C70H131N19O15/c1-17-40(11)55(75)69(103)88-53(35-54(74)90)68(102)87-52(34-39(9)10)67(101)83-46(25-19-22-28-71)62(96)78-45(16)61(95)86-50(32-37(5)6)65(99)79-42(13)58(92)77-43(14)60(94)85-51(33-38(7)8)66(100)80-44(15)59(93)81-47(26-20-23-29-72)63(97)82-48(27-21-24-30-73)64(98)89-56(41(12)18-2)70(104)84-49(57(76)91)31-36(3)4/h36-53,55-56H,17-35,71-73,75H2,1-16H3,(H2,74,90)(H2,76,91)(H,77,92)(H,78,96)(H,79,99)(H,80,100)(H,81,93)(H,82,97)(H,83,101)(H,84,104)(H,85,94)(H,86,95)(H,87,102)(H,88,103)(H,89,98)/t40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,55-,56-/m0/s1

InChI key

MASXKPLGZRMBJF-MVSGICTGSA-N

Gene Information

human ... CALM1(801) , PLA2R1(22925)
mouse ... CALM1(12313) , PLA2R1(18779)
rat ... CALM1(24242) , PLA2R1(295631)

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Amino Acid Sequence

Ile-Asn-Leu-Lys-Ala-Leu-Ala-Ala-Leu-Ala-Lys-Lys-Ile-Leu-NH2

General description

Mastoparan is a cationic, amphiphilic, tetradecapeptide amide. It is composed of the restricted amino acid and the repeated sequence. This protein is a nonspecific secretagogue isolated from venom of wasp.

Application

Mastoparan has been used as a calmodulin antagonist.

Biochem/physiol Actions

Mast cell degranulating peptide. Activates phospholipase A2; inhibits calmodulin. Cell permeable; stimulates exocytosis and phosphoinositide breakdown.
Mastoparan effectively stimulates exocytosis from diverse mammalian cells. The encoded protein facilitates the secretion of histamine from mast cells, serotonin from platelets, catecholamines from chromaffin cells and prolactin from the anterior pituitary. In addition, it is also involved in activation of Phospholipase A2 and phosphoinositides (Pl) break down. Mastoparan functions as an inhibitor for calmodulin-stimulated phosphodiesterase. Mastoparan helps in mitochondrial permeability transition by enhancing an apparent bimodal mechanism of action.

Other Notes

Lyophilized from 0.1% TFA in H2O

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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A new mast cell degranulating peptide "mastoparan" in the venom of Vespula lewisii.
Y Hirai et al.
Chemical & pharmaceutical bulletin, 27(8), 1942-1944 (1979-08-01)
K M Clapp et al.
American journal of physiology. Heart and circulatory physiology, 304(5), H660-H666 (2013-01-22)
Statin drugs inhibit 3-hydroxy-3-methylglutaryl CoA reductase, which reduces the synthesis of both cholesterol and isoprenoids (geranylgeranyl pyrophosphate and farnesyl pyrophosphate), with the latter being lipid molecules responsible for the posttranslational modification of small GTP-binding proteins such as Rho. Effects of
Sarah Jones et al.
Bioconjugate chemistry, 23(1), 47-56 (2011-12-14)
Retro-inverso transformation has commonly been employed as a strategy both for the synthesis of proteolytically stable peptide analogues and for the detailed investigation of structure activity relationships. Herein, we adopted a similar strategy to probe the structure activity relationships of
Lauri Tõntson et al.
Archives of biochemistry and biophysics, 524(2), 93-98 (2012-06-05)
Recombinant heterotrimeric G-protein α(i1), α(i2) and α(i3) subunits were purified in GDP-depleting conditions by affinity chromatography using StrepII-tagged β₁γ₂ subunits. Real-time monitoring of fluorescence anisotropy of Bodipy-FL-GTPγS was used for characterization of nucleotide binding properties and inactivation of the purified
Inhibition of calmodulin activity by insect venom peptides
Barnette MS
Biochemical Pharmacology, 32, 2929-2933 (1983)
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