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M5280

Mastoparan, Vespula lewisii

Name: Mastoparan, <I>Vespula lewisii</I>
Brand: SIGMA

≥97% (HPLC), powder

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About This Item

Empirical Formula (Hill Notation):

C₇₀H₁₃₁N₁₉O₁₅

CAS Number:

72093-21-1

Molecular Weight:

1478.91

UNSPSC Code:

41106300

NACRES:

NA.32

PubChem Substance ID:

329818006

MDL number:

MFCD00076865

Beilstein/REAXYS Number:

5491949

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Properties

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)

Description

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

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.

Mast cell degranulating peptide. Activates phospholipase A₂; inhibits calmodulin. Cell permeable; stimulates exocytosis and phosphoinositide breakdown.

Other Notes

Lyophilized from 0.1% TFA in H2O

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Enantiomer-specific bioactivities of peptidomimetic analogues of mastoparan and mitoparan: characterization of inverso mastoparan as a highly efficient cell penetrating peptide.

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

The Rho kinase inhibitor Y-27632 increases erythrocyte deformability and low oxygen tension-induced ATP release.

K M Thuet et al.

American journal of physiology. Heart and circulatory physiology, 301(5), H1891-H1896 (2011-09-06)

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

Single-transmembrane domain IGF-II/M6P receptor: potential interaction with G protein and its association with cholesterol-rich membrane domains.

Asha Amritraj et al.

Endocrinology, 153(10), 4784-4798 (2012-08-21)

The IGF-II/mannose 6-phosphate (M6P) receptor is a single-transmembrane domain glycoprotein that plays an important role in the intracellular trafficking of lysosomal enzymes and endocytosis-mediated degradation of IGF-II. The receptor may also mediate certain biological effects in response to IGF-II binding

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Global Trade Item Number

SKU	GTIN
M5280-1MG	04061826739013
M5280-5MG	04061833421239