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Prepro VIP (81-122), human

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It is the 81-122 amino acid fragment of prepro-vasoactive intestinal polypeptide (VIP). Peptide histidine valine 42 (PHV-42) has been specified to precisely correspond to Prepro VIP (81-122), which reduces the force and frequency of spontaneous uterine contractions in isolated rats.

Category

Peptide Inhibitors

Catalog number

BAT-010598

CAS number

111366-38-2

Molecular Formula

C202H325N53O64S

Molecular Weight

4552.13

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)-6-amino-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]hexanoyl]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)-1-[[2-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-4-carboxy-1-[[(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]-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-2-oxoethyl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

Synonyms

His-Ala-Asp-Gly-Val-Phe-Thr-Ser-Asp-Phe-Ser-Lys-Leu-Leu-Gly-Gln-Leu-Ser-Ala-Lys-Lys-Tyr-Leu-Glu-Ser-Leu-Met-Gly-Lys-Arg-Val-Ser-Ser-Asn-Ile-Ser-Glu-Asp-Pro-Val-Pro-Val; L-histidyl-L-alanyl-L-alpha-aspartyl-glycyl-L-valyl-L-phenylalanyl-L-threonyl-L-seryl-L-alpha-aspartyl-L-phenylalanyl-L-seryl-L-lysyl-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-methionyl-glycyl-L-lysyl-L-arginyl-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; peptide histidine valine 42; Preprovasoactive intestinal peptide (81-122); Prepro-vip (81-122)

Appearance

White or Off-white Lyophilized Powder

Purity

>98%

Sequence

HADGVFTSDFSKLLGQLSAKKYLESLMGKRVSSNISEDPVPV

Storage

Store at -20°C

InChI

InChI=1S/C202H325N53O64S/c1-25-107(20)161(197(314)246-142(94-260)188(305)227-123(59-62-152(270)271)174(291)240-137(85-156(278)279)199(316)254-70-41-52-145(254)193(310)250-159(105(16)17)200(317)255-71-42-53-146(255)194(311)251-160(106(18)19)201(318)319)252-185(302)134(82-148(209)266)237-190(307)141(93-259)244-192(309)144(96-262)245-196(313)158(104(14)15)249-176(293)121(51-40-69-213-202(210)211)224-169(286)117(47-32-36-65-203)220-149(267)87-214-166(283)125(64-72-320-24)228-178(295)128(75-100(6)7)234-189(306)140(92-258)241-175(292)124(60-63-153(272)273)226-177(294)127(74-99(4)5)233-181(298)132(80-113-54-56-115(264)57-55-113)235-172(289)119(49-34-38-67-205)223-170(287)118(48-33-37-66-204)222-163(280)109(22)219-186(303)138(90-256)242-180(297)130(77-102(10)11)232-173(290)122(58-61-147(208)265)221-150(268)88-215-167(284)126(73-98(2)3)230-179(296)129(76-101(8)9)231-171(288)120(50-35-39-68-206)225-187(304)139(91-257)243-182(299)131(78-111-43-28-26-29-44-111)236-183(300)136(84-155(276)277)238-191(308)143(95-261)247-198(315)162(110(23)263)253-184(301)133(79-112-45-30-27-31-46-112)239-195(312)157(103(12)13)248-151(269)89-216-168(285)135(83-154(274)275)229-164(281)108(21)218-165(282)116(207)81-114-86-212-97-217-114/h26-31,43-46,54-57,86,97-110,116-146,157-162,256-264H,25,32-42,47-53,58-85,87-96,203-207H2,1-24H3,(H2,208,265)(H2,209,266)(H,212,217)(H,214,283)(H,215,284)(H,216,285)(H,218,282)(H,219,303)(H,220,267)(H,221,268)(H,222,280)(H,223,287)(H,224,286)(H,225,304)(H,226,294)(H,227,305)(H,228,295)(H,229,281)(H,230,296)(H,231,288)(H,232,290)(H,233,298)(H,234,306)(H,235,289)(H,236,300)(H,237,307)(H,238,308)(H,239,312)(H,240,291)(H,241,292)(H,242,297)(H,243,299)(H,244,309)(H,245,313)(H,246,314)(H,247,315)(H,248,269)(H,249,293)(H,250,310)(H,251,311)(H,252,302)(H,253,301)(H,270,271)(H,272,273)(H,274,275)(H,276,277)(H,278,279)(H,318,319)(H4,210,211,213)/t107-,108-,109-,110+,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,157-,158-,159-,160-,161-,162-/m0/s1

InChI Key

BNIWRYZWNKLPMV-SYRUQPPYSA-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)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCCN)NC(=O)CNC(=O)C(CCSC)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(CC3=CC=C(C=C3)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(CCCCN)NC(=O)C(CO)NC(=O)C(CC4=CC=CC=C4)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(CC5=CC=CC=C5)NC(=O)C(C(C)C)NC(=O)CNC(=O)C(CC(=O)O)NC(=O)C(C)NC(=O)C(CC6=CN=CN6)N

1.Isolation, characterization, and pharmacological actions of peptide histidine valine 42, a novel prepro-vasoactive intestinal peptide-derived peptide.

Yiangou Y1, Di Marzo V, Spokes RA, Panico M, Morris HR, Bloom SR. J Biol Chem. 1987 Oct 15;262(29):14010-3.

The primary structure and biological activity of a novel prepro-vasoactive intestinal peptide (prepro-VIP)-derived peptide has been determined from an adrenal pheochromocytoma. The peptide was purified sufficiently for characterization by fast atom bombardment mapping after cation-exchange and reverse-phase fast protein liquid chromatography. The sequence of this novel peptide corresponds exactly to prepro-VIP-81-122 and has been designated peptide histidine valine 42 (PHV-42). Synthetic PHV-42 reduced both the force and frequency of spontaneous contractions of isolated rat uterus and was at least 12 times more potent than peptide histidine methionine (prepro-VIP-81-107), and over a hundred times more potent than noradrenaline. PHV-42 was also more potent than peptide histidine methionine in relaxing smooth muscle preparations of rat stomach and guinea pig trachea, but was approximately 4-fold less potent in reducing blood pressure than VIP.