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(β-Asp5)-delta-Sleep Inducing Peptide

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

(β-Asp5)-delta-Sleep Inducing Peptide, a DSIP analog, is a good substrate for the protein L-isoaspartyl methyltransferase, an enzyme occuring in the brain involved in repairing age-damaged proteins containing atypical iosaspartyl peptide bonds.

Category

Others

Catalog number

BAT-015078

CAS number

82602-88-8

Molecular Formula

C35H48N10O15

Molecular Weight

848.81

Specification
Reference Reading

IUPAC Name

(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(3S)-3-[[2-[[2-[[(2S)-2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]propanoyl]amino]acetyl]amino]acetyl]amino]-3-carboxypropanoyl]amino]propanoyl]amino]-3-hydroxypropanoyl]amino]acetyl]amino]pentanedioic acid

Synonyms

(β-Asp5)-Delta-Sleep Inducing Peptide (rabbit); H-Trp-Ala-Gly-Gly-Asp(Ala-Ser-Gly-Glu-OH)-OH; L-Tryptophyl-L-alanylglycylglycyl-L-β-aspartyl-L-alanyl-L-serylglycyl-L-glutamic acid; (3S,9S,12S,16S,25S,28S)-28-amino-9-(hydroxymethyl)-29-(1H-indol-3-yl)-12,25-dimethyl-5,8,11,14,18,21,24,27-octaoxo-4,7,10,13,17,20,23,26-octaazanonacosane-1,3,16-tricarboxylic acid; 5-Isoasp-delta sleep-inducing peptide

Appearance

White or Off-white Lyophilized Powder

Purity

≥95%

Density

1.5±0.1 g/cm3

Boiling Point

1526.5±65.0°C at 760 mmHg

Sequence

H2N-WAGG-βAsp-ASGE-OH

Storage

Store at -20°C

InChI

InChI=1S/C35H48N10O15/c1-16(42-32(55)20(36)9-18-11-37-21-6-4-3-5-19(18)21)30(53)39-12-26(48)38-13-27(49)44-23(35(59)60)10-25(47)41-17(2)31(54)45-24(15-46)33(56)40-14-28(50)43-22(34(57)58)7-8-29(51)52/h3-6,11,16-17,20,22-24,37,46H,7-10,12-15,36H2,1-2H3,(H,38,48)(H,39,53)(H,40,56)(H,41,47)(H,42,55)(H,43,50)(H,44,49)(H,45,54)(H,51,52)(H,57,58)(H,59,60)/t16-,17-,20-,22-,23-,24-/m0/s1

InChI Key

GGEQPJVCJLUAOE-GFVHOAGBSA-N

Canonical SMILES

CC(C(=O)NC(CO)C(=O)NCC(=O)NC(CCC(=O)O)C(=O)O)NC(=O)CC(C(=O)O)NC(=O)CNC(=O)CNC(=O)C(C)NC(=O)C(CC1=CNC2=CC=CC=C21)N

1. Delta-sleep-inducing peptide (DSIP): an update

M V Graf, A J Kastin Peptides. 1986 Nov-Dec;7(6):1165-87. doi: 10.1016/0196-9781(86)90148-8.

The isolation and characterization of delta-sleep-inducing peptide (DSIP) achieved from 1963 to 1977 were reviewed in 1984. The first reports describing sleep as well as extra-sleep effects of DSIP also were included in that work. Only two years later, much additional literature concerning DSIP has accumulated. Besides further sleep-inducing and/or -supporting effects of DSIP in animals, considerable work has been carried out to evaluate the potential use of the peptide for therapeutic purposes such as treatment of insomnia, pain, and withdrawal. Immunohistochemical as well as radioimmunochemical studies provided further insights into the natural occurrence of the nonpeptide and the distribution of DSIP-like material in the body, suggesting possible relations of the peptide to certain diseases. Various physiological functions of DSIP and a possible mechanism of action involving the modulation of adrenergic transmission remain to be established.

2. Delta-sleep-inducing peptide (DSIP): a review

M V Graf, A J Kastin Neurosci Biobehav Rev. 1984 Spring;8(1):83-93. doi: 10.1016/0149-7634(84)90022-8.

Since the turn of the century, it has been postulated that humoral factors induce sleep. Many compounds were proposed as sleep-factors, but only two of the sleep-peptides have been purified to homogeneity and characterized, so far. One of them, DSIP, was shown to be a nonapeptide of MW 849 and to induce mainly delta-sleep in rabbits, rats, mice, and humans, whereas in cats, the effect on REM sleep was more pronounced. A U-shaped activity curve was determined for the dose as well as for the time of infusion. DSIP-like material was found by RIA and immunohistochemistry in brain and by RIA in peripheral organs of the rat as well as in plasma of several mammals. In addition to sleep, the peptide also has been observed to affect electrophysiological activity, neurotransmitter levels in the brain, circadian and locomotor patterns, hormonal levels, psychological performance, and the activity of neuropharmacological drugs including their withdrawal.