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Prepro VIP (111-122), human

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It is the 111-122 amino acid fragment of prepro-vasoactive intestinal polypeptide (VIP). VIP is present in the peripheral and central nervous system as a non-adrenergic, non-cholinergic neurotransmitter or neuromodulator.

Category

Peptide Inhibitors

Catalog number

BAT-010597

CAS number

123025-94-5

Molecular Formula

C53H87N13O21

Molecular Weight

1242.33

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-2-[[(2S,3S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-4-oxobutanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-5-[[(2S)-3-carboxy-1-[(2S)-2-[[(2S)-1-[(2S)-2-[[(1S)-1-carboxy-2-methylpropyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

Synonyms

PHM/VIP (Spacer Peptide); Preprovasoactive intestinal peptide (111-122); Val-Ser-Ser-Asn-Ile-Ser-Glu-Asp-Pro-Val-Pro-Val; L-valyl-L-seryl-L-seryl-L-asparagyl-L-isoleucyl-L-seryl-L-alpha-glutamyl-L-alpha-aspartyl-L-prolyl-L-valyl-L-prolyl-L-valine; N-(1-(N-(1-(N-(N-(N-(N-(N2-(N-(N-L-Valyl-L-seryl)-L-seryl)-L-asparginyl)-L-isoleucyl)-L-seryl)-L-alpha-glutamyl)-L-alpha-aspartyl)-L-propyl)-L-valyl)-L-propyl)-L-valine

Appearance

White or Off-white Lyophilized Powder

Purity

95%

Density

1.4±0.1 g/cm3

Boiling Point

1700.7±65.0°C at 760 mmHg

Sequence

VSSNISEDPVPV

Storage

Store at -20°C

InChI

InChI=1S/C53H87N13O21/c1-9-26(8)41(64-43(76)28(18-35(54)70)57-45(78)30(20-67)59-46(79)31(21-68)60-49(82)38(55)23(2)3)50(83)61-32(22-69)44(77)56-27(14-15-36(71)72)42(75)58-29(19-37(73)74)51(84)65-16-10-12-33(65)47(80)62-39(24(4)5)52(85)66-17-11-13-34(66)48(81)63-40(25(6)7)53(86)87/h23-34,38-41,67-69H,9-22,55H2,1-8H3,(H2,54,70)(H,56,77)(H,57,78)(H,58,75)(H,59,79)(H,60,82)(H,61,83)(H,62,80)(H,63,81)(H,64,76)(H,71,72)(H,73,74)(H,86,87)/t26-,27-,28-,29-,30-,31-,32-,33-,34-,38-,39-,40-,41-/m0/s1

InChI Key

HKKDGJFKJBWDQK-FYKWFVNCSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CO)C(=O)NC(CCC(=O)O)C(=O)NC(CC(=O)O)C(=O)N1CCCC1C(=O)NC(C(C)C)C(=O)N2CCCC2C(=O)NC(C(C)C)C(=O)O)NC(=O)C(CC(=O)N)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(C(C)C)N

1. Location of PHM/VIP mRNA in human gastrointestinal tract detected by in situ hybridization

P C Emson, B S Wulff, J Fahrenkrug, H E Bredkjaer Cell Tissue Res . 1994 May;276(2):229-38. doi: 10.1007/BF00306108.

The expression of the gene for vasoactive intestinal polypeptide (VIP) and peptide histidine methionine (PHM) in the human gastrointestinal tract was studied by in situ hybridization and Northern blotting for PHM/VIP mRNA and immunocytochemistry using specific antisera against the bioactive peptides PHM and VIP. In the colon sigmoideum, antisera against all five putative processing products of the VIP precursor (prepro-VIP) were used, namely prepro-VIP 22-79, PHM, prepro-VIP 111-122, VIP and prepro-VIP 156-170. Furthermore, RNA extracted from various regions of the gastrointestinal tract was examined by Northern blots and hybridization to a VIP-cDNA probe. Throughout the gastrointestinal tract, PHM/VIP mRNA was found in neurons only. Using single- or double-staining methods, we demonstrated both PHM/VIP mRNA and the corresponding peptides PHM and VIP in the neurons. In the sigmoideum, the single-staining methods were extended to investigate whether the neurons simultaneously contained PHM/VIP mRNA and each of the five prepro-VIP-derived peptides. Only one major band of PHM/VIP mRNA (1.9 kb) was found by Northern blotting in the tissue of the gastrointestinal tract.

2. Characterization and regional distribution of peptides derived from the vasoactive intestinal peptide precursor in the normal human brain

P C Emson, J Fahrenkrug J Neurochem . 1989 Oct;53(4):1142-8. doi: 10.1111/j.1471-4159.1989.tb07407.x.

To study the biosynthetic processing of the precursor for vasoactive intestinal peptide (prepro-VIP) in the human brain, we have developed antisera against the five functional domains of the precursor molecule: prepro-VIP 22-79, peptide histidine methionine (PHM), prepro-VIP 111-122, VIP, and prepro-VIP 156-170. The antisera were used in radioimmunoassays in combination with HPLC to identify and quantify the peptides in regions of the human brain. All five peptides were expressed, but mainly in nonequimolar ratios. In only three regions were the same amounts of VIP and PHM found; in the remaining areas the concentration of PHM was two-thirds that of VIP. The concentrations of prepro-VIP 22-79, prepro-VIP 111-122, and prepro-VIP 156-170 were considerably lower than the corresponding VIP concentrations, and the relative concentration of prepro-VIP 111-122 differed between cortical and subcortical areas. A small proportion of the VIP precursor followed a pathway in which the dibasic conversion site after PHM is not cleaved, as evidenced by the presence of a C-terminally extended form of PHM. Finally, it was found that the C-terminal lysine residue of prepro-VIP is not removed during processing. The findings indicate that differences in the posttranslational processing of prepro-VIP exist in subpopulations of neurons in the human brain.

3. Neuropeptides in the human penis: an immunohistochemical study

A H Graf, J Frick, D Mack, O Dietze, F Sundler, G W Hacker, C Hauser-Kronberger J Androl . 1994 Nov-Dec;15(6):510-20.

In the present study, the distribution of neuropeptides in the human penis is demonstrated by immunohistochemistry (IHC). IHC screening detected a complex network of nerve fibers containing vasoactive intestinal polypeptide (VIP), peptide histidine-methionine (PHM), prepro-VIP (111-122), neuropeptide Y (NPY), C-flanking peptide of NPY (C-PON), calcitonin gene-related peptide, substance P, and galanin immunoreactivities. Special attention was also given to the recently isolated, VIP-related lizard peptide helospectin, which could also be detected in neuronal elements in the penis. Colocalization studies showed the coexistence of VIP, PHM, and partly helospectin, and of NPY with C-PON within nerve fibers in the cavernous and spongious body, the glans penis, and the urethra.