Need Assistance?

US & Canada:
+
UK: +

FAQs

Resources

Our Highlights

GMP Grade Efficient workshop for GMP production.
Optimal Prices Buying products on this site guarantees the best price!
Commercial Batches Independent GMP manufacturing suites that handle commercial batches
Prompt Delivery Warehouses in multiple cities to ensure timely delivery
Flexible Quantity Quantities available from milligrams to ton

Application Area

N-Acetyl-α-Endorphin

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

N-Acetyl-α-Endorphin is the N-terminal acetylated α-Endorphi, which is an endogenous opioid peptide.

Category

Peptide Inhibitors

Catalog number

BAT-009289

CAS number

88264-63-5

Molecular Formula

C79H122N18O27S

Molecular Weight

1787.98

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-5-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S,3R)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(1S,2R)-1-carboxy-2-hydroxypropyl]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]-5-oxopentanoic acid

Synonyms

N-Acetyl-Alpha-Endorphin; alpha-N-Acetyl-alpha-endorphin; α-Endorphin (sheep), N-acetyl-; Ac-Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr; N-acetyl-L-tyrosyl-glycyl-glycyl-L-phenylalanyl-L-methionyl-L-threonyl-L-seryl-L-alpha-glutamyl-L-lysyl-L-seryl-L-glutaminyl-L-threonyl-L-prolyl-L-leucyl-L-valyl-L-threonine

Purity

≥95%

Density

1.3±0.1 g/cm3

Boiling Point

2124.0±65.0°C at 760 mmHg

Sequence

Ac-YGGFMTSEKSQTPLVT

Storage

Store at -20°C

Solubility

Soluble in Water, DMSO

InChI

InChI=1S/C79H122N18O27S/c1-39(2)32-52(72(116)93-62(40(3)4)76(120)96-65(43(7)102)79(123)124)90-75(119)57-19-15-30-97(57)78(122)64(42(6)101)95-69(113)49(24-26-58(81)105)87-73(117)55(37-98)91-67(111)48(18-13-14-29-80)86-68(112)50(25-27-61(108)109)88-74(118)56(38-99)92-77(121)63(41(5)100)94-70(114)51(28-31-125-9)89-71(115)54(33-45-16-11-10-12-17-45)85-60(107)36-82-59(106)35-83-66(110)53(84-44(8)103)34-46-20-22-47(104)23-21-46/h10-12,16-17,20-23,39-43,48-57,62-65,98-102,104H,13-15,18-19,24-38,80H2,1-9H3,(H2,81,105)(H,82,106)(H,83,110)(H,84,103)(H,85,107)(H,86,112)(H,87,117)(H,88,118)(H,89,115)(H,90,119)(H,91,111)(H,92,121)(H,93,116)(H,94,114)(H,95,113)(H,96,120)(H,108,109)(H,123,124)

InChI Key

OAEFPDJOJNEWON-UHFFFAOYSA-N

Canonical SMILES

CC(C)CC(C(=O)NC(C(C)C)C(=O)NC(C(C)O)C(=O)O)NC(=O)C1CCCN1C(=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(CC2=CC=CC=C2)NC(=O)CNC(=O)CNC(=O)C(CC3=CC=C(C=C3)O)NC(=O)C

1. N-acetyl endorphin in rat spermatogonia and primary spermatocytes

M C Cheng, J A Clements, A I Smith, S J Lolait, J W Funder J Clin Invest. 1985 Mar;75(3):832-5. doi: 10.1172/JCI111779.

In previous reports modest levels of beta-endorphin have been found by radioimmunoassay in rat testis, and localized by immunofluorescence to the interstitial cells. We have confirmed these previous reports and extended them by showing that the majority of testicular endorphins are acetylated forms, N-acetyl gamma-endorphin, N-acetyl alpha-endorphin, and N-acetyl beta-endorphin1-27. In addition, N-acetylated endorphins are not found in interstitial cells, but are confined to spermatogonia and primary spermatocytes.

2. Characterization of N alpha-acetyl-alpha-endorphin from rat neurointermediate lobe and its distribution in pituitary and brain

V M Wiegant, J Verhoef, J P Burbach, A van Amerongen Life Sci. 1983;33 Suppl 1:125-8. doi: 10.1016/0024-3205(83)90460-5.

N alpha-Acetyl-alpha-endorphin was characterized from rat neurointermediate lobe. The distribution of the acetylated and the non-acetylated form of alpha-endorphin in dissected areas of pituitary and brain appeared to be uneven. alpha-Endorphin appeared to be the main peptide in the anterior pituitary, whereas in the neurointermediate lobe N alpha-acetyl-alpha-endorphin accounted for most of the alpha-endorphin immunoreactivity. In the brain, the highest concentration of alpha-endorphin immunoreactivity was found in the hypothalamus. In hypothalamus and thalamus alpha-endorphin predominated, whereas in amygdala, hippocampus and septum N alpha-acetyl-alpha-endorphin represented most of the alpha-endorphin-immunoreactivity. In view of the non-opioid properties of acetylated endorphins, it is suggested that acetylation represents a mechanism allowing the organism to specifically select the non-opioid behavioral activities enclosed in the endorphin sequence.

3. Identification of N alpha-acetyl-alpha-endorphin and N alpha-acetyl-gamma-endorphin isolated from the neurointermediate lobe of the rat pituitary gland

J P Burbach, H H Van Tol, V M Wiegant, R A Van Ooijen, R A Maes J Biol Chem. 1985 Jun 10;260(11):6663-9.

The peptides that represent the major components with alpha-endorphin- and gamma-endorphin-like immunoreactivity in the rat neurointermediate lobe were purified to homogeneity and chemically characterized. Rat neurointermediate lobes were extracted by boiling and homogenization in acetic acid. Peptide purification was based on gel filtration, followed by two high-pressure liquid chromatography steps. Pools containing peptides with the size and immunochemical properties of alpha- and gamma-endorphins were resolved by reverse-phase high-pressure liquid chromatography into multiple immunoreactive components. The major forms were finally purified by paired-ion high-pressure liquid chromatography. The amino acid compositions of these peptides fitted the beta-endorphin sequences 1-16 and 1-17. Tryptic mapping, aminopeptidase M digestion, chromatographic characterization, and immunoreactivity to an antiserum recognizing the N alpha-acetylated terminus of endorphins showed that these peptides were indistinguishable from N alpha-acetyl-alpha-endorphin (N alpha-acetyl-beta-endorphin 1-16), and N alpha-acetyl-gamma-endorphin (N alpha-acetyl-beta-endorphin 1-17). The NH2-terminal residue of the peptides was identified by mass spectrometry as N alpha-acetyltyrosine, substantiating the identity of the peptides. The results demonstrate the existence of N alpha-acetylated alpha- and gamma-endorphin as endogenous peptides in the neurointermediate lobe of the rat pituitary gland. In view of their occurrence and biological properties they should be considered significant members of the pro-opiomelanocortin family.