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Peptide YY, human

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Peptide YY (PYY) is an intestinal hormone secreted by neuroendocrine cells in the ileum and colon and has been shown to reduce appetite.

Category

Peptide Inhibitors

Catalog number

BAT-010016

CAS number

118997-30-1

Molecular Formula

C194H295N55O57

Molecular Weight

4309.81

Specification
Reference Reading

IUPAC Name

(4S)-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-[[2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S,3S)-2-[[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylpentanoyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-4-carboxybutanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-5-oxopentanoic acid

Synonyms

PYY; Peptide YY; C16118

Appearance

Solid

Purity

≥97% by HPLC

Sequence

YPIKPEAPGEDASPEELNRYYASLRHYLNLVTRQRY

Storage

Store at -20°C

InChI

InChI=1S/C194H295N55O57/c1-17-99(12)154(244-183(299)143-36-25-73-247(143)188(304)115(196)80-104-37-47-110(253)48-38-104)185(301)228-125(28-18-19-67-195)189(305)248-74-26-34-141(248)181(297)225-122(59-64-149(264)265)159(275)218-102(15)187(303)246-72-24-33-140(246)180(296)214-90-147(261)219-120(58-63-148(262)263)164(280)240-137(88-152(270)271)169(285)217-101(14)158(274)242-139(92-251)190(306)249-75-27-35-142(249)182(298)226-124(61-66-151(268)269)166(282)224-123(60-65-150(266)267)167(283)230-128(77-95(4)5)171(287)238-135(86-145(198)259)176(292)222-117(30-21-69-211-192(203)204)162(278)234-132(83-107-43-53-113(256)54-44-107)174(290)235-131(82-106-41-51-112(255)52-42-106)168(284)216-100(13)157(273)241-138(91-250)179(295)233-127(76-94(2)3)170(286)221-118(31-22-70-212-193(205)206)163(279)237-134(85-109-89-209-93-215-109)175(291)236-133(84-108-45-55-114(257)56-46-108)173(289)231-129(78-96(6)7)172(288)239-136(87-146(199)260)177(293)232-130(79-97(8)9)178(294)243-153(98(10)11)184(300)245-155(103(16)252)186(302)227-119(32-23-71-213-194(207)208)160(276)223-121(57-62-144(197)258)165(281)220-116(29-20-68-210-191(201)202)161(277)229-126(156(200)272)81-105-39-49-111(254)50-40-105/h37-56,89,93-103,115-143,153-155,250-257H,17-36,57-88,90-92,195-196H2,1-16H3,(H2,197,258)(H2,198,259)(H2,199,260)(H2,200,272)(H,209,215)(H,214,296)(H,216,284)(H,217,285)(H,218,275)(H,219,261)(H,220,281)(H,221,286)(H,222,292)(H,223,276)(H,224,282)(H,225,297)(H,226,298)(H,227,302)(H,228,301)(H,229,277)(H,230,283)(H,231,289)(H,232,293)(H,233,295)(H,234,278)(H,235,290)(H,236,291)(H,237,279)(H,238,287)(H,239,288)(H,240,280)(H,241,273)(H,242,274)(H,243,294)(H,244,299)(H,245,300)(H,262,263)(H,264,265)(H,266,267)(H,268,269)(H,270,271)(H4,201,202,210)(H4,203,204,211)(H4,205,206,212)(H4,207,208,213)/t99-,100-,101-,102-,103+,115-,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-,153-,154-,155-/m0/s1

InChI Key

YNXLOPYTAAFMTN-SBUIBGKBSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CCCCN)C(=O)N1CCCC1C(=O)NC(CCC(=O)O)C(=O)NC(C)C(=O)N2CCCC2C(=O)NCC(=O)NC(CCC(=O)O)C(=O)NC(CC(=O)O)C(=O)NC(C)C(=O)NC(CO)C(=O)N3CCCC3C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC4=CC=C(C=C4)O)C(=O)NC(CC5=CC=C(C=C5)O)C(=O)NC(C)C(=O)NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC6=CNC=N6)C(=O)NC(CC7=CC=C(C=C7)O)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(C(C)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCC(=O)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC8=CC=C(C=C8)O)C(=O)N)NC(=O)C9CCCN9C(=O)C(CC1=CC=C(C=C1)O)N

1. Expression of peptide YY in human brain and pituitary tissues

Takashi Suzuki, Kazuhiro Takahashi, Sadayoshi Ito, Fumitoshi Satoh, Kazuhito Totsune, Osamu Murakami, Ryo Morimoto, Masayuki Saruta, Hironobu Sasano Nutrition . 2008 Sep;24(9):878-84. doi: 10.1016/j.nut.2008.06.011.

Expression of peptide YY (PYY) in the human brain and pituitary tissues was studied by radioimmunoassay, immunocytochemistry, and reverse transcription polymerase chain reaction. The polyclonal antibody raised against human PYY(1-36) in a rabbit was used in the assay, which showed 100% cross-reactivity with PYY(3-36) and no significant cross-reactivity with other peptides including neuropeptide Y and pancreatic polypeptide. The highest concentration of immunoreactive PYY was found in the hypothalamus (0.44+/-0.060 pmol/g of wet weight, mean +/- SEM, n=8), followed by the pituitary (0.41+/-0.16 pmol/g of wet weight, n=3). Reverse-phase high performance liquid chromatography of tissue extracts of human rectum and cortical brain showed a peak eluted in the position of authentic PYY(1-36) and PYY(3-36). Immunocytochemistry showed positive immunostaining for PYY in neurons of the paraventricular, arcuate, and supraoptic nuclei of the human hypothalamus. Moreover, reverse transcription polymerase chain reaction analysis showed expression of mRNA for PYY in human brain and pituitary tissues. The present study has shown for the first time expression of PYY in the human brain and pituitary tissues, suggesting a role for PYY as a neurotransmitter, in the neuroendocrine physiology, such as regulation of appetite and energy expenditure and modulation of pituitary hormone secretion.

2. The Role of Neuropeptide Y and Peptide YY in the Development of Obesity via Gut-brain Axis

Xi Ma, Zhibin Cheng, Yi Wu, Yueyu Bai, Hengxun He Curr Protein Pept Sci . 2019;20(7):750-758. doi: 10.2174/1389203720666190125105401.

Obesity is one of the main challenges of public health in the 21st century. Obesity can induce a series of chronic metabolic diseases, such as diabetes, dyslipidemia, hypertension and nonalcoholic fatty liver, which seriously affect human health. Gut-brain axis, the two-direction pathway formed between enteric nervous system and central nervous system, plays a vital role in the occurrence and development of obesity. Gastrointestinal signals are projected through the gut-brain axis to nervous system, and respond to various gastrointestinal stimulation. The central nervous system regulates visceral activity through the gut-brain axis. Brain-gut peptides have important regulatory roles in the gut-brain axis. The brain-gut peptides of the gastrointestinal system and the nervous system regulate the gastrointestinal movement, feeling, secretion, absorption and other complex functions through endocrine, neurosecretion and paracrine to secrete peptides. Both neuropeptide Y and peptide YY belong to the pancreatic polypeptide family and are important brain-gut peptides. Neuropeptide Y and peptide YY have functions that are closely related to appetite regulation and obesity formation. This review describes the role of the gutbrain axis in regulating appetite and maintaining energy balance, and the functions of brain-gut peptides neuropeptide Y and peptide YY in obesity. The relationship between NPY and PYY and the interaction between the NPY-PYY signaling with the gut microbiota are also described in this review.

3. Peptide YY

Keval Chandarana, Rachel Batterham Curr Opin Endocrinol Diabetes Obes . 2008 Feb;15(1):65-72. doi: 10.1097/MED.0b013e3282f3f4b1.

Purpose of review:This review discusses recent studies examining the effects of peptide YY on energy homeostasis, highlights the emerging hedonic effects of peptide YY and evaluates the therapeutic potential of the peptide YY system.Recent findings:A role for exogenous PYY3-36 as an anorectic agent in obese humans and rodents has been established and weight loss effects demonstrated in obese rodents. New lines of evidence support a role for endogenous peptide YY in regulating energy homeostasis. The NPY-Y2 receptor mediates the anorectic actions of PYY3-36 with rodent studies implicating the hypothalamus, vagus and brainstem as key target sites. Functional imaging in humans has confirmed that PYY3-36 activates brainstem and hypothalamic regions. The greatest effects, however, were observed within the orbitofrontal cortex, a brain region involved in reward processing. Further evidence for a hedonic role for PYY3-36 is supported by rodent studies showing that PYY3-36 decreases the motivation to seek high-fat food. Rodent studies using selective Y2 agonists and strategies combining PYY3-36/Y2 agonists with other anorectic agents have revealed increased anorectic and weight-reducing effects.Summary:Peptide YY plays a role in the integrative regulation of metabolism. The emerging hedonic effects of peptide YY together with the weight-reducing effects observed in obese rodents suggest that targeting the peptide YY system may offer a therapeutic strategy for obesity.