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PHI-27 (porcine)

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

PHI-27 (porcine) belongs to the glucagon-secretin family and plays a key role in the generation of circadian oscillations. It has bioactivity similar to vasoactive intestinal peptide (VIP) and secretin.

Category

Peptide Inhibitors

Catalog number

BAT-015183

CAS number

80458-29-3

Molecular Formula

C136H216N36O40

Molecular Weight

2995.39

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]propanoyl]amino]-3-carboxypropanoyl]amino]acetyl]amino]-3-methylbutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-5-oxopentanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]hexanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-5-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-amino-3-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

Synonyms

PHI (PHI-27), porcine; H-His-Ala-Asp-Gly-Val-Phe-Thr-Ser-Asp-Phe-Ser-Arg-Leu-Leu-Gly-Gln-Leu-Ser-Ala-Lys-Lys-Tyr-Leu-Glu-Ser-Leu-Ile-NH2; L-histidyl-L-alanyl-L-alpha-aspartyl-glycyl-L-valyl-L-phenylalanyl-L-threonyl-L-seryl-L-alpha-aspartyl-L-phenylalanyl-L-seryl-L-arginyl-L-leucyl-L-leucyl-glycyl-L-glutaminyl-L-leucyl-L-seryl-L-alanyl-L-lysyl-L-lysyl-L-tyrosyl-L-leucyl-L-alpha-glutamyl-L-seryl-L-leucyl-L-isoleucinamide

Appearance

White Lyophilized Powder

Purity

≥95%

Density

1.44±0.1 g/cm3 (Predicted)

Sequence

HADGVFTSDFSRLLGQLSAKKYLESLI-NH2

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C136H216N36O40/c1-18-73(14)109(111(141)188)171-128(205)92(52-71(10)11)161-132(209)100(64-175)166-121(198)87(42-44-105(182)183)155-122(199)89(49-68(4)5)160-125(202)94(55-79-37-39-81(178)40-38-79)162-118(195)84(35-26-28-46-138)153-117(194)83(34-25-27-45-137)152-112(189)75(16)150-130(207)98(62-173)167-124(201)91(51-70(8)9)159-120(197)86(41-43-102(140)179)151-103(180)60-146-115(192)88(48-67(2)3)157-123(200)90(50-69(6)7)158-119(196)85(36-29-47-145-136(142)143)154-131(208)99(63-174)168-126(203)93(53-77-30-21-19-22-31-77)163-127(204)97(58-107(186)187)164-133(210)101(65-176)169-135(212)110(76(17)177)172-129(206)95(54-78-32-23-20-24-33-78)165-134(211)108(72(12)13)170-104(181)61-147-116(193)96(57-106(184)185)156-113(190)74(15)149-114(191)82(139)56-80-59-144-66-148-80/h19-24,30-33,37-40,59,66-76,82-101,108-110,173-178H,18,25-29,34-36,41-58,60-65,137-139H2,1-17H3,(H2,140,179)(H2,141,188)(H,144,148)(H,146,192)(H,147,193)(H,149,191)(H,150,207)(H,151,180)(H,152,189)(H,153,194)(H,154,208)(H,155,199)(H,156,190)(H,157,200)(H,158,196)(H,159,197)(H,160,202)(H,161,209)(H,162,195)(H,163,204)(H,164,210)(H,165,211)(H,166,198)(H,167,201)(H,168,203)(H,169,212)(H,170,181)(H,171,205)(H,172,206)(H,182,183)(H,184,185)(H,186,187)(H4,142,143,145)/t73-,74-,75-,76+,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,108-,109-,110-/m0/s1

InChI Key

HVIBDEARFMWSND-WNKXUTMESA-N

Canonical SMILES

CCC(C)C(C(=O)N)NC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CC1=CC=C(C=C1)O)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(C)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)N)NC(=O)CNC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CO)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(C(C)C)NC(=O)CNC(=O)C(CC(=O)O)NC(=O)C(C)NC(=O)C(CC4=CN=CN4)N

1. A C-terminally elongated form of PHI from porcine intestine

E Eriste, D Nepomuceno, R Sillard, A Norberg, T W Lovenberg, H Jörnvall, V Bonetto Cell Mol Life Sci . 1999 Nov 15;56(7-8):709-13. doi: 10.1007/s000180050464.

A C-terminally elongated form of peptide histidine isoleucine amide (PHI) was isolated from porcine intestine based on its effect on cAMP production in IMR-32 cells. The structure was determined by amino acid sequence analysis of tryptic fragments and by mass spectrometry. The peptide has 42 amino acid residues like those described from human, rat and mouse, but the amino acid sequence of the C-terminal extension of pig PHI is unique. Unlike the other peptides, it has a C-terminal Ala and it differs at five positions from the human form and at six positions from the rat form, while the human and the rat forms differ by only two substitutions. To avoid confusion arising from different C-terminal residues, a unifying nomenclature is proposed: PHI-27 for the hormone and PHI-42 for the elongated product.

2. The distribution and chromatographic characterization of PHI (peptide histidine isoleucine amide)-27-like peptides in rat and porcine brain

M C Beinfeld, B L Roth, D M Korchak, T L O'Donohue J Neurosci . 1984 Nov;4(11):2681-8. doi: 10.1523/JNEUROSCI.04-11-02681.1984.

This study was initiated to characterize PHI (peptide histidine isoleucine amide)-27-like peptides (PLPs) in rat and porcine brain in comparison with other members of the vasoactive intestinal polypeptide (VIP) family and to investigate their distribution by radioimmunoassay. The peptidic nature of the rat brain PLP was indicated by its trypsin sensitivity. On Sephadex chromatography rat brain PLP has the same molecular weight as synthetic (porcine intestinal) PHI-27. High pressure liquid chromatographic separations revealed that PLP in rat and porcine brain extracts elutes as a single peak distinct from VIP or secretin. Porcine brain PLP elutes in the same position as synthetic PHI-27, whereas rat brain PLP immunoreactivity consistently separates from synthetic PHI-27. This suggests that porcine brain PLP is identical to synthetic PHI-27, in agreement with the reported sequence of Tatemoto et al. (Tatemoto, K., M. Carlquist, T. McDonald, and V. Mutt (1983) FEBS Lett. 153: 248-252), whereas PLP may have a different amino acid sequence (or may be post-translationally modified). Using specific PHI and VIP radioimmunoassays, the distribution of PLP was found to parallel that of VIP in rat and porcine brain, being highest in cerebral cortex, amygdala, and hippocampus. PLP, like VIP, is abundant in rat retina and can be included in the growing list of retinal peptides. This highly correlated distribution of VIP and PLP may be explained by the recent discovery that they are derived from the same precursor (Itoh, N., K. Obata, N. Yanaihara, and H. Okamoto (1983) Nature 304: 547-549).(ABSTRACT TRUNCATED AT 250 WORDS)

3. Human preprovasoactive intestinal polypeptide contains a novel PHI-27-like peptide, PHM-27

N Yanaihara, K Obata, H Okamoto, N Itoh Nature . 1983 Aug;304(5926):547-9. doi: 10.1038/304547a0.

Vasoactive intestinal polypeptide (VIP), a 28-amino acid peptide originally isolated from porcine duodenum, is present not only in gastrointestinal tissues but also in neural tissues, possibly as a neurotransmitter, and exhibits a wide range of biological actions (for example, relaxation of smooth muscle, stimulation of intestinal water and electrolyte secretion and release of insulin, glucagon and several anterior pituitary hormones). As the structure of porcine and bovine VIP shows several similarities to those of mammalian glucagon, secretin and gastric inhibitory peptide (GIP), VIP is considered to be a member of the glucagon-secretin family. Recently, we have found that VIP is synthesized from a precursor, pro-VIP (molecular weight (Mr) 17,500), in human neuroblastoma cells and that the primary translation product of the mRNA encoding VIP is prepro-VIP (Mr 20,000). In an attempt to elucidate the primary structure of the precursor, we have now cloned the DNA sequence complementary to the mRNA coding for human VIP and analysed the nucleotide sequence. The entire amino acid sequence of the precursor, deduced from the nucleotide sequence, indicates that the precursor protein contains not only VIP but also a novel peptide of 27 amino acids. The peptide, designated PHM-27, differs by only 2 amino acids from PHI-27, a peptide recently isolated from porcine intestine, and is also closely related in sequence to VIP.