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β-Endorphin (6-31) (human)

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

β-Endorphin (6-31) (human) is a fragment of β-endorphin that retains the C-terminal. It acts as a non-opioid β-endorphin antagonist, and mediates effects on the immune system.

Category

Peptide Inhibitors

Catalog number

BAT-014429

CAS number

77761-27-4

Molecular Formula

C131H218N34O40

Molecular Weight

2909.38

Specification
Reference Reading

IUPAC Name

(2S)-2-[[2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-6-amino-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-amino-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-4-carboxybutanoyl]amino]hexanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxybutanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-4-oxobutanoyl]amino]propanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]-4-oxobutanoyl]amino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]hexanoyl]amino]hexanoyl]amino]acetyl]amino]pentanedioic acid

Synonyms

H-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-Ile-Lys-Asn-Ala-Tyr-Lys-Lys-Gly-Glu-OH; L-threonyl-L-seryl-L-alpha-glutamyl-L-lysyl-L-seryl-L-glutaminyl-L-threonyl-L-prolyl-L-leucyl-L-valyl-L-threonyl-L-leucyl-L-phenylalanyl-L-lysyl-L-asparagyl-L-alanyl-L-isoleucyl-L-isoleucyl-L-lysyl-L-asparagyl-L-alanyl-L-tyrosyl-L-lysyl-L-lysyl-glycyl-L-glutamic acid; b-Endorphin (6-31)

Appearance

White Lyophilized Powder

Purity

≥90%

Sequence

TSEKSQTPLVTLFKNAIIKNAYKKGE

Storage

Store at -20°C

InChI

InChI=1S/C131H218N34O40/c1-16-68(9)103(127(200)151-82(38-25-30-54-136)112(185)155-90(60-96(138)173)116(189)142-70(11)107(180)152-88(59-76-40-42-77(171)43-41-76)119(192)147-79(35-22-27-51-133)110(183)145-78(34-21-26-50-132)109(182)141-62-98(175)144-85(131(204)205)46-49-100(178)179)162-128(201)104(69(10)17-2)161-108(181)71(12)143-117(190)91(61-97(139)174)154-111(184)80(36-23-28-52-134)148-120(193)89(58-75-32-19-18-20-33-75)153-118(191)86(56-65(3)4)157-129(202)105(73(14)169)163-126(199)102(67(7)8)160-121(194)87(57-66(5)6)156-124(197)94-39-31-55-165(94)130(203)106(74(15)170)164-115(188)83(44-47-95(137)172)149-122(195)92(63-166)158-113(186)81(37-24-29-53-135)146-114(187)84(45-48-99(176)177)150-123(196)93(64-167)159-125(198)101(140)72(13)168/h18-20,32-33,40-43,65-74,78-94,101-106,166-171H,16-17,21-31,34-39,44-64,132-136,140H2,1-15H3,(H2,137,172)(H2,138,173)(H2,139,174)(H,141,182)(H,142,189)(H,143,190)(H,144,175)(H,145,183)(H,146,187)(H,147,192)(H,148,193)(H,149,195)(H,150,196)(H,151,200)(H,152,180)(H,153,191)(H,154,184)(H,155,185)(H,156,197)(H,157,202)(H,158,186)(H,159,198)(H,160,194)(H,161,181)(H,162,201)(H,163,199)(H,164,188)(H,176,177)(H,178,179)(H,204,205)/t68-,69-,70-,71-,72+,73+,74+,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,101-,102-,103-,104-,105-,106-/m0/s1

InChI Key

WCOFQMXJGOCODK-JXBHHXAKSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CC(=O)N)C(=O)NC(C)C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(CCC(=O)O)C(=O)O)NC(=O)C(C)NC(=O)C(CC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CC(C)C)NC(=O)C(C(C)O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C3CCCN3C(=O)C(C(C)O)NC(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)N

1. Beta-endorphin and lipopolysaccharide interactions with human neutrophils

C O Simpkins, E Tate, S Alailima J Natl Med Assoc. 1988 Feb;80(2):199-203.

The binding of the Escherichia coli peptide, N-formyl methionyl leucyl phenylalanine (FMLP), to human neutrophils was found to be reduced by E coli lipopolysaccharide (LPS). This reduction is reversed by human β-endorphin 1-31. β-Endorphin (BE) also increased the binding of FMLP in the absence of LPS. Structural analogs of BE, namely BE 1-27 and N-acetyl BE 1-31, were equal to BE in potency. BE 6-31, however, was less potent than BE. These effects may be mediated by a neutrophil binding site for BE, which was found to have a K(D) of 4.1 × 10(7) and 315,930 sites per cell. These findings provide an explanation for the authors' previous observation that BE enhances the chemotaxis of neutrophils toward FMLP. Furthermore, these data suggest that there may be a role for BE in the modulation of neutrophilic function in the septic state.

2. Effects of beta-endorphin fragment 6-31 on morphine- and beta-endorphin-induced growth hormone and prolactin release

A E Panerai, D Cocchi, M Parenti, A Martini, P Mantegazza, C H Li Eur J Pharmacol. 1984 Apr 6;99(4):341-3. doi: 10.1016/0014-2999(84)90143-2.

A fragment of human beta-endorphin (beta h-EP-(6-31] has been proposed as an endogenous inhibitor of beta-endorphin. We have evaluated the effects of the fragment on beta-endorphin- and morphine-induced prolactin and growth hormone release. It inhibited both morphine- and beta-endorphin-induced prolactin release, while it was ineffective on the release of growth hormone.

3. Interaction of human beta-endorphin with nonopiate binding sites on the terminal SC5b-9 complex of human complement. Significance of COOH-terminal beta H-endorphin fragments

L Schweigerer, H Teschemacher, S Bhakdi, M Lederle J Biol Chem. 1983 Oct 25;258(20):12287-92.

We have characterized the binding of 125I-labeled human beta-endorphin (125I-beta H-endorphin) to sites present on the terminal fluid-phase complex of human complement, consisting of complement components C5b, C6, C7, C8, C9, and the S-protein (SC5b-9 complex). Specific binding exhibited saturability, reversibility, structural specificity, temperature dependence, and absence of negative cooperative effects. Binding was maximal at 4 degrees C and pH 7.0; it was diminished by monovalent and divalent cations as well as by increasing concentrations of urea and Triton X-100 and apparently required intact disulfide groups. Binding was not inhibited by a number of opioid peptides sharing common sequences with the NH2 terminus of beta H-endorphin. In contrast, binding was inhibited by beta H-endorphin, N-acetyl-beta H-endorphin, and a series of COOH-terminal beta H-endorphin fragments, where of the COOH-terminal dipeptide Gly-Glu represented the minimal effective structure. Stepwise extension towards the NH2 terminus led to an increased binding affinity of the respective fragment. Computer resolution of competition curves yielded one binding component for several shorter COOH-terminal beta H-endorphin fragments and for beta H-endorphin (1-5) + (16-31), whereas two distinct binding components were obtained when beta H-endorphin (27-31), beta H-endorphin (6-31), N-acetyl-beta H-endorphin or beta H-endorphin were used as inhibitors. This study presents detailed data on the binding of COOH-terminal beta H-endorphin fragments to specific nonopiate binding sites present on the terminal SC5b-9 complex of human complement. We suggest that through this interaction, beta H-endorphin may modulate certain functions within the immune system.