[Des-octanoyl]-Ghrelin, human

Product Name: [Des-octanoyl]-Ghrelin, human

Sequence One Letter Code: GSSFLSPEHQRVQQRKESKKPPAKLQPR

Sequence Three Letter Code: H-Gly-Ser-Ser-Phe-Leu-Ser-Pro-Glu-His-Gln-Arg-Val-Gln-Gln-Arg-Lys-Glu-Ser-Lys-Lys-Pro-Pro-Ala-Lys-Leu-Gln-Pro-Arg-OH

Cas No: 313951-59-6

Chemical Formula:C141H235N47O41

Molecular Weight: 3244.9

Purity: 95%

Form: Lyophilized

Storage Conditions: - 20 °C

Research Area: Endocrinology Disease Research

SMILES: C[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]3CCCN3C(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC4=CNC=N4)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H]5CCCN5C(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC6=CC=CC=C6)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)CN

IUPAC: (4S)-4-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]amino]-5-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-6-amino-1-[(2S)-2-[(2S)-2-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-5-amino-1-[(2S)-2-[[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl]pyrrolidin-1-yl]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxopropan-2-yl]carbamoyl]pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

INCHIKEY: BGHSOEHUOOAYMY-JTZMCQEISA-N

INCHI:

InChI=1S/C141H235N47O41/c1-73(2)62-92(123(213)175-90(42-48-107(150)196)135(225)185-58-22-37-102(185)132(222)176-91(138(228)229)34-21-57-160-141(155)156)177-116(206)79(28-11-15-51-142)164-112(202)76(7)162-130(220)100-35-24-60-187(100)137(227)103-38-25-61-188(103)134(224)89(31-14-18-54-145)174-115(205)81(30-13-17-53-144)168-128(218)97(69-190)181-121(211)87(43-49-109(198)199)170-113(203)80(29-12-16-52-143)165-114(204)82(32-19-55-158-139(151)152)166-117(207)84(39-45-104(147)193)169-119(209)86(41-47-106(149)195)173-133(223)111(75(5)6)184-122(212)83(33-20-56-159-140(153)154)167-118(208)85(40-46-105(148)194)171-126(216)95(65-78-67-157-72-161-78)180-120(210)88(44-50-110(200)201)172-131(221)101-36-23-59-186(101)136(226)99(71-192)183-124(214)93(63-74(3)4)178-125(215)94(64-77-26-9-8-10-27-77)179-129(219)98(70-191)182-127(217)96(68-189)163-108(197)66-146/h8-10,26-27,67,72-76,79-103,111,189-192H,11-25,28-66,68-71,142-146H2,1-7H3,(H2,147,193)(H2,148,194)(H2,149,195)(H2,150,196)(H,157,161)(H,162,220)(H,163,197)(H,164,202)(H,165,204)(H,166,207)(H,167,208)(H,168,218)(H,169,209)(H,170,203)(H,171,216)(H,172,221)(H,173,223)(H,174,205)(H,175,213)(H,176,222)(H,177,206)(H,178,215)(H,179,219)(H,180,210)(H,181,211)(H,182,217)(H,183,214)(H,184,212)(H,198,199)(H,200,201)(H,228,229)(H4,151,152,158)(H4,153,154,159)(H4,155,156,160)/t76-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,111-/m0/s1

Source / Species: human

Conjugation: Unconjugated

Code Nacres: NA.26

Application: Des-octanoyl (des-acyl) Ghrelin is the unacylated form of the human peptide hormone ghrelin, generated when the n-octanoyl modification on the serine residue is absent. This lipid modification is essential for activation of the growth hormone secretagogue receptor GHSR1a, and therefore des-acyl ghrelin does not function as a classical GHSR1a agonist. Despite lacking this receptor activity, des-acyl ghrelin is the predominant circulating form of ghrelin in plasma and has attracted significant research interest due to its distinct biological effects. Scientific studies suggest that des-acyl ghrelin participates in metabolic regulation, appetite and energy balance, cardiovascular protection, and cellular survival pathways through mechanisms that may involve alternative receptors or receptor-independent signaling. Because of these properties, des-acyl ghrelin is widely used as a research peptide for investigating the broader ghrelin signaling network and for studying physiological processes related to metabolism, cardiovascular function, and cell regulation.

Current Research: Ghrelin is widely recognized as a key peptide hormone involved in appetite regulation, energy balance, and endocrine signaling. First discovered in 1999, ghrelin functions primarily through activation of the growth hormone secretagogue receptor (GHSR1a), a G-protein–coupled receptor that stimulates growth hormone release and influences metabolic processes. Classical ghrelin activity depends on a unique post-translational modification: the attachment of an n-octanoyl fatty acid to the serine residue at position three. However, when this lipid modification is absent, the peptide exists as des-octanoyl ghrelin, commonly referred to as des-acyl ghrelin. Although des-acyl ghrelin cannot activate GHSR1a, it has become an increasingly important molecule in metabolic and physiological research. In fact, des-acyl ghrelin represents the major circulating form of ghrelin in plasma, often accounting for the majority of total ghrelin detected in blood samples. Its abundance, combined with its unexpected biological activities, has prompted extensive investigation into alternative ghrelin signaling pathways. Structural Characteristics and Formation Des-acyl ghrelin is produced when the enzyme ghrelin O-acyltransferase (GOAT) does not attach the octanoyl group to the serine residue during ghrelin maturation. Without this acyl modification, the peptide cannot bind or activate the canonical receptor GHSR1a. Historically, this led researchers to assume that des-acyl ghrelin was biologically inactive. However, later studies demonstrated that the peptide retains multiple physiological activities independent of classical ghrelin receptor signaling. These discoveries shifted the perception of des-acyl ghrelin from a simple metabolic byproduct to a distinct signaling molecule with its own biological roles. Role in Metabolic Regulation One of the most actively studied aspects of des-acyl ghrelin is its involvement in metabolic regulation. While acylated ghrelin is known for stimulating appetite and promoting energy intake, des-acyl ghrelin appears to exert counter-regulatory or modulatory effects in several metabolic contexts. Experimental studies suggest that des-acyl ghrelin may influence: Glucose metabolism Insulin sensitivity Adipocyte differentiation Lipid metabolism In some models, des-acyl ghrelin has been shown to improve glucose handling and reduce lipid accumulation, suggesting potential roles in metabolic homeostasis and energy balance. These observations have made the peptide relevant in research areas such as obesity, diabetes, and metabolic syndrome. Cardiovascular and Cytoprotective Effects Beyond metabolic signaling, des-acyl ghrelin has demonstrated protective effects in cardiovascular and cellular systems. Several studies indicate that the peptide may contribute to cardioprotection, particularly under conditions of cellular stress. Reported experimental observations include: Protection of cardiomyocytes from apoptosis Reduction of oxidative stress in vascular tissues Support of endothelial cell survival Modulation of inflammatory responses in cardiovascular models These cytoprotective properties suggest that des-acyl ghrelin may participate in mechanisms that help maintain vascular integrity and cardiac function, especially during ischemic or metabolic stress conditions. Alternative Signaling Pathways A central question in current ghrelin biology is how des-acyl ghrelin mediates its effects without activating GHSR1a. Several hypotheses have emerged to explain this phenomenon. Researchers have proposed that des-acyl ghrelin may act through: Alternative or unidentified receptors Receptor heterodimer interactions Receptor-independent intracellular signaling mechanisms Evidence suggests that des-acyl ghrelin may influence pathways involved in cell survival, mitochondrial function, and metabolic signaling, including PI3K/Akt and ERK pathways. While the precise receptor mechanisms remain unresolved, these findings support the concept that ghrelin biology involves multiple parallel signaling networks rather than a single receptor pathway. Implications for Ghrelin Research The growing recognition of des-acyl ghrelin’s biological functions has significantly expanded the scope of ghrelin research. Instead of viewing ghrelin signaling solely through the lens of appetite stimulation, researchers now investigate the broader ghrelin peptide system, including the balance between acylated and des-acyl forms. Des-acyl ghrelin is therefore widely used in experimental studies aimed at understanding: Hormonal control of metabolism Peptide regulation of energy balance Cellular stress response mechanisms Cardiovascular signaling pathways Interactions between endocrine and metabolic systems Because it represents the dominant circulating form of ghrelin, des-acyl ghrelin provides valuable insight into how peptide hormones can exert diverse physiological effects beyond their primary receptor targets. Conclusion Des-acyl ghrelin has evolved from being considered an inactive ghrelin fragment to becoming a key research molecule in metabolic and cardiovascular biology. Despite lacking the acyl modification required for activation of the classical ghrelin receptor GHSR1a, the peptide exhibits a range of biological activities that influence metabolism, cellular survival, and cardiovascular function. Ongoing research continues to explore the mechanisms underlying these effects, particularly the possibility of alternative receptors or receptor-independent signaling pathways. As understanding of the ghrelin signaling network expands, des-acyl ghrelin remains an important tool for investigating the complex interplay between endocrine peptides, metabolism, and cellular regulation.