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Application Area

PACAP-Related Peptide (PRP), human

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

It is a 29 amino-acid region of the PACAP precursor protein.

Category

Others

Catalog number

BAT-009323

Molecular Formula

C139H229N41O42

Molecular Weight

3146.55

Specification
Reference Reading

IUPAC Name

(4S)-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(1S)-1-carboxyethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-carboxypropanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]acetyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-oxopentanoic acid

Synonyms

Asp-Val-Ala-His-Gly-Ile-Leu-Asn-Glu-Ala-Tyr-Arg-Lys-Val-Leu-Asp-Gln-Leu-Ser-Ala-Gly-Lys-His-Leu-Gln-Ser-Leu-Val-Ala

Purity

≥95%

Sequence

DVAHGILNEAYRKVLDQLSAGKHLQSLVA

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C139H229N41O42/c1-23-72(18)111(177-104(188)59-152-116(199)94(51-78-56-148-62-153-78)166-114(197)75(21)157-134(217)108(69(12)13)178-115(198)81(142)53-106(191)192)137(220)174-91(48-67(8)9)124(207)171-96(54-102(145)186)129(212)164-87(38-41-105(189)190)117(200)156-74(20)113(196)165-93(50-77-32-34-80(183)35-33-77)127(210)161-84(31-28-44-150-139(146)147)119(202)160-83(30-25-27-43-141)122(205)179-110(71(16)17)136(219)173-90(47-66(6)7)125(208)172-97(55-107(193)194)130(213)163-85(36-39-100(143)184)120(203)167-89(46-65(4)5)126(209)176-98(60-181)132(215)155-73(19)112(195)151-58-103(187)159-82(29-24-26-42-140)118(201)170-95(52-79-57-149-63-154-79)128(211)168-88(45-64(2)3)123(206)162-86(37-40-101(144)185)121(204)175-99(61-182)133(216)169-92(49-68(10)11)131(214)180-109(70(14)15)135(218)158-76(22)138(221)222/h32-35,56-57,62-76,81-99,108-111,181-183H,23-31,36-55,58-61,140-142H2,1-22H3,(H2,143,184)(H2,144,185)(H2,145,186)(H,148,153)(H,149,154)(H,151,195)(H,152,199)(H,155,215)(H,156,200)(H,157,217)(H,158,218)(H,159,187)(H,160,202)(H,161,210)(H,162,206)(H,163,213)(H,164,212)(H,165,196)(H,166,197)(H,167,203)(H,168,211)(H,169,216)(H,170,201)(H,171,207)(H,172,208)(H,173,219)(H,174,220)(H,175,204)(H,176,209)(H,177,188)(H,178,198)(H,179,205)(H,180,214)(H,189,190)(H,191,192)(H,193,194)(H,221,222)(H4,146,147,150)/t72-,73-,74-,75-,76-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,108-,109-,110-,111-/m0/s1

InChI Key

PEKIUJBTZYWHQI-WXARMGCUSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC(C)C)C(=O)NC(CC(=O)N)C(=O)NC(CCC(=O)O)C(=O)NC(C)C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)O)C(=O)NC(CCC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(C)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CC2=CN=CN2)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(CO)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(C)C(=O)O)NC(=O)CNC(=O)C(CC3=CN=CN3)NC(=O)C(C)NC(=O)C(C(C)C)NC(=O)C(CC(=O)O)N

1. PACAP-related peptide (PRP)--molecular evolution and potential functions

Janice K V Tam, Leo T O Lee, Billy K C Chow Peptides. 2007 Sep;28(9):1920-9. doi: 10.1016/j.peptides.2007.07.011. Epub 2007 Jul 17.

PACAP-related peptide (PRP) and PACAP are structurally related peptides that are encoded in the same transcripts. In the past, it was believed that the mammalian PRPs are evolved from GHRHs in non-mammals. With the recent discovery of authentic GHRH and receptor genes in frog and fish, this review aims to (1) coin the name of all GHRH-like peptides in previous literature as PRPs and (2) provide the background for new research direction for PRP in vertebrates. As a goldfish receptor highly specific for PRP with distinct tissue distribution has previously been characterized, it is highly possible that PRP plays a physiological role in non-mammalian vertebrates and the function of PRP has somehow been lost in mammals as a consequence of the loss of its receptor in the genome. This information may provide clues to elucidate functions of PRP in the future.

2. Molecular cloning and mRNA distribution of pituitary adenylate cyclase-activating polypeptide (PACAP)/PACAP-related peptide in the lungfish

L T O Lee, J K V Tam, D W Chan, B K C Chow Ann N Y Acad Sci. 2009 Apr;1163:209-14. doi: 10.1111/j.1749-6632.2008.03661.x.

In this article, we report the isolation of a full-length cDNA clone encoding pituitary adenylate cyclase-activating polypeptide (PACAP)/PACAP-related peptide (PRP) from lungfish Protopterus dolloi. When comparing the deduced amino acid sequences, the lungfish PACAP was found to be highly conserved with other vertebrates; however, the PRP shares only lower levels of sequence identity with known PRP sequences. Consistently in phylogenetic analysis, the lungfish PRP, similar to sturgeon PRP, fails to cluster with other PRPs. In addition to the full-length clone, another cDNA encoding a short precursor that lacks the first 32 amino acids of the PRP was also isolated. Interestingly, similar isoforms were also identified in several nonmammalian vertebrates, and it was suggested that exon skipping of PRP/PACAP transcripts was a mechanism that regulated the expression ratio of PACAP to PRP in nonmammalian vertebrates. By real-time PCR, both long and short PRP/PACAP transcripts were found almost exclusively in the brain, and the short isoform is the more abundant transcript (3.7 times more), indicating that PACAP is the major product produced in lungfish brain. The expression patterns of lungfish and previously studied frog PRP/PACAP suggest that the PRP/PACAP gene in the tetrapod lineage may first express in the central nervous system; in the process of evolution, the functions of these peptides diversified and were later found in other tissues.

3. VIP and PACAP

Jan Fahrenkrug Results Probl Cell Differ. 2010;50:221-34. doi: 10.1007/400_2009_24.

Vasoactive intestinal polypeptide (VIP) is derived from a 170 amino acid precursor which in addition is processed to preproVIP 22-79, PHI, preproVIP 111-122 and preproVIP 156-170. All preproVIP-derived peptides have been shown in normal tissue and VIP-producing cell lines and elevated quantities occur in plasma and tumour tissues from patients with VIP-producing tumours. In some tissues the dibasic cleavage site after PHI is uncleaved resulting in a C-terminally extended form, PHV. PHI and VIP are present in a 1:1 molar ratio in large dense core vesicles and released in roughly equimolar amounts. Carboxyamidation of VIP and PHI is not critical and glycine-extended forms of both peptides have been demonstrated. Pituitary adenylate cyclase activating polypeptide (PACAP) is derived from a 170 amino acid long precursor, which gives rise to PACAP 38, PACAP 27 and PACAP related peptide (PRP). All peptides are present in tissue, the dominating form being PACAP 38. Prohormone convertase (PC) 1 and 2 seem to be involved in the processing of PACAP, except in the testes and ovary, where the PACAP precursor is substrate for PC4.