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E6136

Sigma-Aldrich

α-Endorphin human

≥97% (HPLC)

Synonym(s):

β-Lipotropin (61-76), human, synthetic, β-Lipotropin 61-76, LPH (61-76), Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr

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About This Item

Empirical Formula (Hill Notation):
C77H120N18O26S
CAS Number:
59004-96-5
Molecular Weight:
1745.95
MDL number:
MFCD00076381
UNSPSC Code:
12352200
PubChem Substance ID:
24894621

assay

≥97% (HPLC)

UniProt accession no.

P01189

storage temp.

−20°C

SMILES string

CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc2ccc(O)cc2)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(O)=O

InChI

1S/C77H120N18O26S/c1-38(2)31-51(70(113)91-60(39(3)4)74(117)94-63(42(7)100)77(120)121)88-73(116)55-18-14-29-95(55)76(119)62(41(6)99)93-67(110)48(23-25-56(80)102)85-71(114)53(36-96)89-65(108)47(17-12-13-28-78)84-66(109)49(24-26-59(105)106)86-72(115)54(37-97)90-75(118)61(40(5)98)92-68(111)50(27-30-122-8)87-69(112)52(33-43-15-10-9-11-16-43)83-58(104)35-81-57(103)34-82-64(107)46(79)32-44-19-21-45(101)22-20-44/h9-11,15-16,19-22,38-42,46-55,60-63,96-101H,12-14,17-18,23-37,78-79H2,1-8H3,(H2,80,102)(H,81,103)(H,82,107)(H,83,104)(H,84,109)(H,85,114)(H,86,115)(H,87,112)(H,88,116)(H,89,108)(H,90,118)(H,91,113)(H,92,111)(H,93,110)(H,94,117)(H,105,106)(H,120,121)/t40-,41-,42-,46+,47+,48+,49+,50+,51+,52+,53+,54+,55+,60+,61+,62+,63+/m1/s1

InChI key

NXSIJWJXMWBCBX-NWKQFZAZSA-N

Gene Information

human ... POMC(5443)

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Amino Acid Sequence

Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr

General description

α-Endorphin is one of the three endorphins found in the brain, which has morphine-mimetic activities. It is a hexadecapeptide with a primary structure of H-Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-SerGln-Thr-Pro-Leu-Val-Thr-OH.[1] It is a fragment of β-Endorphin (β-LPH61-91), which is an endogenous opioid ligand, and is denoted as (β-LPH61-76).[2] It is found in the hypothalamus and pituitary.[3]

Biochem/physiol Actions

α-Endorphin is a substrate for transglutaminase[4], and has stimulatory effects on immune system function.[5] It influences the self-stimulating tendencies in rat, related to electrical stimulation of the ventral tegmentum area neurons. It counteracts the effect of γ-endorphin and promotes this behavior in rats.[6] The functionality of α-endorphin is comparable to that of psychostimulant drugs, and as it acts in an opposing manner to γ-endorphin, these peptides might have a central role in the homeostasis of brain function.[2]

Other Notes

Lyophilized from 0.1% TFA in H2O

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
043M4781V
091M4804V
059K4848
117K4790
026K4779

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J P Burbach et al.
Nature, 283(5742), 96-97 (1980-01-03)
beta-Endorphin (beta-LPH61-91) is a well known endogenous opioid ligand. It and related peptides have recently been implicated in the control of adaptive behaviour. Smaller beta-endorphin fragments appeared to be more active moieties than the parent molecule in a number of
P van den Bergh et al.
Cellular immunology, 154(1), 109-122 (1994-03-01)
The presence of the opioid peptides alpha- and beta-endorphin (-End) but not methionine enkephalin (Met-enk) in in vitro cultures of purified CD4+ T cells, stimulated with concanavalin A in the presence of irradiated spleen cells, resulted in a threefold stimulation
Effects of [Des-Tyr 1]-gamma-endorphin and alpha-endorphin on substantia nigra self-stimulation.
D M Dorsa et al.
Pharmacology, biochemistry, and behavior, 10(6), 899-905 (1979-06-01)
P Sacerdote et al.
Peptides, 10(3), 565-569 (1989-05-01)
We evaluated the chemotactic activity of beta-endorphin and beta-endorphin-related peptides on human monocytes. We tested beta-endorphin(1-31) and fragments (1-16), (1-17), (1-27) in which the N-terminal of the opioid is preserved, N-acetyl-beta-endorphin(1-31) and fragments (6-31) and (28-31) in which the C-terminal
B Bucher et al.
European journal of pharmacology, 147(2), 305-308 (1988-03-01)
Isolated rat tail arteries were perfused and vasoconstriction was evoked by electrical field stimulation (2 pulses at 1 Hz every 2 min). The vasoconstriction was depressed by DAGO (IC50 = 611 nM) and beta-endorphin (IC50 = 37 nM). Structuraly analogues
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