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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/REAXYS Number:
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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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K M Thuet et al.
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Low oxygen (O(2)) tension and mechanical deformation are stimuli for ATP release from erythrocytes. It has been shown previously that rabbit erythrocytes made less deformable with diamide, a thiol cross-linking agent, release less ATP in response to low O(2) tension
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Activation of Phospholipase A2 by Auxin and Mastoparan in Hypocotyl Segments from Zucchini and Sunflower
Scherer GFE
Journal of Plant Physiology, 145, 483-490 (1995)
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