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Application Area

beta-endorphin (1-27), human

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

β-Endorphin (1-27) is an endogenous peptide.

Category

Others

Catalog number

BAT-010711

CAS number

76622-84-9

Molecular Formula

C139H217N33O40S

Molecular Weight

3022.5

Specification
Reference Reading

IUPAC Name

5-[[6-amino-1-[[1-[[5-amino-1-[[1-[2-[[1-[[1-[[1-[[1-[[1-[[6-amino-1-[[4-amino-1-[[1-[[1-[[1-[[6-amino-1-[[4-amino-1-[[1-[[1-carboxy-2-(4-hydroxyphenyl)ethyl]amino]-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-[[2-[[2-[[2-[[2-[[2-[[2-[[2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoic acid

Synonyms

beta-Endorphin human fragment 1-27

Purity

≥97% by HPLC

Sequence

YGGFMXSEKSQXPLVXLFKNAXXKNAY (Modifications: X-6 = xiThr, X-12 = xiThr, X-16 = xiThr, X-22 = xiIle, X-23 = xiIle)

InChI

InChI=1S/C139H217N33O40S/c1-17-73(9)110(134(206)157-89(38-27-30-55-142)119(191)160-97(64-104(145)181)124(196)149-75(11)115(187)163-99(139(211)212)63-83-42-46-85(179)47-43-83)168-135(207)111(74(10)18-2)167-116(188)76(12)150-125(197)98(65-105(146)182)159-118(190)87(36-25-28-53-140)153-128(200)96(62-81-34-23-20-24-35-81)158-126(198)93(58-70(3)4)162-136(208)113(78(14)176)170-133(205)109(72(7)8)166-129(201)94(59-71(5)6)161-132(204)102-39-31-56-172(102)138(210)114(79(15)177)171-122(194)90(48-50-103(144)180)154-130(202)100(68-173)164-120(192)88(37-26-29-54-141)152-121(193)91(49-51-108(185)186)155-131(203)101(69-174)165-137(209)112(77(13)175)169-123(195)92(52-57-213-16)156-127(199)95(61-80-32-21-19-22-33-80)151-107(184)67-147-106(183)66-148-117(189)86(143)60-82-40-44-84(178)45-41-82/h19-24,32-35,40-47,70-79,86-102,109-114,173-179H,17-18,25-31,36-39,48-69,140-143H2,1-16H3,(H2,144,180)(H2,145,181)(H2,146,182)(H,147,183)(H,148,189)(H,149,196)(H,150,197)(H,151,184)(H,152,193)(H,153,200)(H,154,202)(H,155,203)(H,156,199)(H,157,206)(H,158,198)(H,159,190)(H,160,191)(H,161,204)(H,162,208)(H,163,187)(H,164,192)(H,165,209)(H,166,201)(H,167,188)(H,168,207)(H,169,195)(H,170,205)(H,171,194)(H,185,186)(H,211,212)

InChI Key

CMLHEPBOBGYCBC-UHFFFAOYSA-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)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)NC(=O)C(CCSC)NC(=O)C(CC4=CC=CC=C4)NC(=O)CNC(=O)CNC(=O)C(CC5=CC=C(C=C5)O)N

1. Chemical synthesis of human beta-endorphin(1-27) analogs by peptide segment coupling. Leucine and glycine residues bearing thiocarboxyl functions as junctions for peptide segment coupling

H C Cheng, D Yamashiro Int J Pept Protein Res. 1991 Jul;38(1):70-8.

[Gly8]beta hEP(1-27)NH2 and [L-Leu8]beta hEP(1-27)NH2, two analogs of human beta-endorphin, were synthesized by both all-stepwise solid phase synthesis and peptide segment coupling. For the peptide segment coupling method, two thiocarboxyl peptides. Msc-[Gly8]beta hEP(1-8)SH and Msc-[L-Leu8]beta hEP(1-8)SH, were synthesized by standard solid phase method on 4-[alpha-(Boc-Gly-S)benzyl]phenoxyacetamidomethy-resin and 4-[alpha-(Boc-L-Leu-S)benzyl]phenoxyacetamidomethy-resin. These two thiocarboxyl peptides were coupled to H-[Lys(Cit)9,19,24]-beta hEP(9-27)NH2. [Gly8]beta hEP(1-27)NH2 and [L-Leu8]beta hEP(1-27)NH2 were obtained after removal of Msc groups and citraconyl groups from products of the segment coupling reaction. The yields of both [Gly8]beta hEP(1-27)NH2 and [L-Leu8]beta hEP(1-27)NH2 in the segment coupling reaction were approximately 18%. Less than 1% of racemization of Leu-8 occurred during coupling of Msc-[L-Leu8]beta hEP(1-8)SH to H-[Lys(Cit)9,19,24]-beta hEP(9-27)NH2. Results of amino acid composition analysis, analysis by reverse phase high pressure liquid chromatography and receptor binding activity assays of the analogs showed that peptide analogs prepared by segment coupling method and those prepared by all-stepwise solid phase synthesis were identical. Results of receptor binding activity assays suggested that the molecular charge properties of beta-endorphin(1-27) and its analogs influenced the receptor binding activity.

2. beta-endorphin-(1-27) is an antagonist of beta-endorphin analgesia

R G Hammonds Jr, P Nicolas, C H Li Proc Natl Acad Sci U S A. 1984 Mar;81(5):1389-90. doi: 10.1073/pnas.81.5.1389.

beta h-Endorphin-(1-27), a naturally occurring fragment of human beta-endorphin (beta h-endorphin), diminishes the analgesic effect of beta h-endorphin when coinjected intra-cerebroventricularly into mice. A parallel shift in the dose-response curve of beta h-endorphin in the presence of beta h-endorphin-(1-27) suggests competition at the same site. The potency of beta h-endorphin-(1-27) in antagonizing analgesia is greater than 4 times greater than that of the opiate antagonist naloxone.

3. alpha N-acetyl derivatives of beta-endorphin-(1-31) and -(1-27) regulate the supraspinal antinociceptive activity of different opioids in mice

J Garzón, P Sánchez-Blázquez Life Sci. 1991;48(14):1417-27. doi: 10.1016/0024-3205(91)90439-i.

alpha N-acetyl human beta-endorphin-(1-31) injected icv to mice antagonized the analgesic activity of beta-endorphin-(1-31) and morphine whereas the analgesia evoked by DADLE and DAGO was enhanced by this treatment. The modulatory activity of alpha N-acetyl beta-endorphin-(1-31) was exhibited at remarkable low doses (fmols) reaching a maximum that persisted even though the dose was increased 100,000 times. The regulatory effect of a single dose of the acetylated neuropeptide lasted for 24h. The activity of alpha N-acetyl human beta-endorphin-(1-31) was partially retained by the shorter peptide alpha N-acetyl human beta-endorphin-(1-27) and to a lesser extent by beta-endorphin-(1-27), beta-endorphin-(1-31) lacked this regulatory activity on opioid analgesia. Acetylated beta-endorphin-(1-31) displayed a biphasic curve when competing with 5 pM [125I]-Tyr27 human beta-endorphin-(1-31) specific binding, the first step (20 to 30% of the binding) was abolished with an apparent IC50 of 0.35 nM, and the rest with an IC50 of 200 nM. It is suggested that alpha N-acetyl beta-endorphin-(1-31) changed the efficiency of the opioid analgesics by acting upon a specific substrate that is functionally coupled to the opioid receptor, presumably the guanine nucleotide binding regulatory proteins Gi/Go.