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GLP-2 (1-34) (human)

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

GLP-2 (1-34) (human) is a human-derived mimic of glucagon-like peptide 2 employed in studying gastrointestinal disorders such as short bowel syndrome (SBS).

Category

Functional Peptides

Catalog number

BAT-015103

CAS number

99120-49-7

Molecular Formula

C171H266N48O56S1

Molecular Weight

3922.29

Specification
Reference Reading

IUPAC Name

(4S)-5-[[(2S)-1-[[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-5-amino-1-[[(2S,3R)-1-[[(2S)-6-amino-1-[[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-[[(1S)-4-carbamimidamido-1-carboxybutyl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-[[(2S)-2-[[(2S)-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-hydroxypropanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-5-oxopentanoic acid

Synonyms

Preproglucagon (146-179) (human); H-His-Ala-Asp-Gly-Ser-Phe-Ser-Asp-Glu-Met-Asn-Thr-Ile-Leu-Asp-Asn-Leu-Ala-Ala-Arg-Asp-Phe-Ile-Asn-Trp-Leu-Ile-Gln-Thr-Lys-Ile-Thr-Asp-Arg-OH; L-histidyl-L-alanyl-L-alpha-aspartyl-glycyl-L-seryl-L-phenylalanyl-L-seryl-L-alpha-aspartyl-L-alpha-glutamyl-L-methionyl-L-asparagyl-L-threonyl-L-isoleucyl-L-leucyl-L-alpha-aspartyl-L-asparagyl-L-leucyl-L-alanyl-L-alanyl-L-arginyl-L-alpha-aspartyl-L-phenylalanyl-L-isoleucyl-L-asparagyl-L-tryptophyl-L-leucyl-L-isoleucyl-L-glutaminyl-L-threonyl-L-lysyl-L-isoleucyl-L-threonyl-L-alpha-aspartyl-L-arginine

Appearance

White Lyophilized Solid

Purity

95%

Sequence

HADGSFSDEMNTILDNLAARDFINWLIQTKITDR

Storage

Store at -20°C

Solubility

Soluble in Acetic Acid

InChI

InChI=1S/C171H266N48O56S/c1-22-80(11)130(162(267)196-99(47-49-119(174)225)146(251)217-134(87(18)222)166(271)195-97(44-34-35-52-172)145(250)213-133(83(14)25-4)165(270)219-135(88(19)223)167(272)211-116(70-129(240)241)154(259)197-102(169(274)275)46-37-54-184-171(180)181)214-157(262)105(58-79(9)10)200-150(255)108(61-92-71-185-96-43-33-32-42-94(92)96)203-152(257)110(64-121(176)227)210-163(268)131(81(12)23-2)215-158(263)107(60-91-40-30-27-31-41-91)201-155(260)114(68-127(236)237)206-142(247)98(45-36-53-183-170(178)179)192-138(243)85(16)188-137(242)84(15)190-147(252)103(56-77(5)6)199-151(256)109(63-120(175)226)205-156(261)115(69-128(238)239)207-148(253)104(57-78(7)8)209-164(269)132(82(13)24-3)216-168(273)136(89(20)224)218-159(264)111(65-122(177)228)204-144(249)101(51-55-276-21)194-143(248)100(48-50-124(230)231)193-153(258)113(67-126(234)235)208-161(266)118(75-221)212-149(254)106(59-90-38-28-26-29-39-90)202-160(265)117(74-220)191-123(229)73-186-141(246)112(66-125(232)233)198-139(244)86(17)189-140(245)95(173)62-93-72-182-76-187-93/h26-33,38-43,71-72,76-89,95,97-118,130-136,185,220-224H,22-25,34-37,44-70,73-75,172-173H2,1-21H3,(H2,174,225)(H2,175,226)(H2,176,227)(H2,177,228)(H,182,187)(H,186,246)(H,188,242)(H,189,245)(H,190,252)(H,191,229)(H,192,243)(H,193,258)(H,194,248)(H,195,271)(H,196,267)(H,197,259)(H,198,244)(H,199,256)(H,200,255)(H,201,260)(H,202,265)(H,203,257)(H,204,249)(H,205,261)(H,206,247)(H,207,253)(H,208,266)(H,209,269)(H,210,268)(H,211,272)(H,212,254)(H,213,250)(H,214,262)(H,215,263)(H,216,273)(H,217,251)(H,218,264)(H,219,270)(H,230,231)(H,232,233)(H,234,235)(H,236,237)(H,238,239)(H,240,241)(H,274,275)(H4,178,179,183)(H4,180,181,184)/t80-,81-,82-,83-,84-,85-,86-,87+,88+,89+,95-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,130-,131-,132-,133-,134-,135-,136-/m0/s1

InChI Key

GMSOBKLEMFCAKA-GHAFJTHLSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(C(C)O)C(=O)NC(CC(=O)O)C(=O)NC(CCCNC(=N)N)C(=O)O)NC(=O)C(CCCCN)NC(=O)C(C(C)O)NC(=O)C(CCC(=O)N)NC(=O)C(C(C)CC)NC(=O)C(CC(C)C)NC(=O)C(CC1=CNC2=CC=CC=C21)NC(=O)C(CC(=O)N)NC(=O)C(C(C)CC)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CC(=O)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(C)NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CC(=O)N)NC(=O)C(CC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(C(C)CC)NC(=O)C(C(C)O)NC(=O)C(CC(=O)N)NC(=O)C(CCSC)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(CC4=CC=CC=C4)NC(=O)C(CO)NC(=O)CNC(=O)C(CC(=O)O)NC(=O)C(C)NC(=O)C(CC5=CN=CN5)N

1. Glucagon-like peptide-1 but not glucagon-like peptide-2 stimulates insulin release from isolated rat pancreatic islets

W Creutzfeldt, W E Schmidt, E G Siegel Diabetologia . 1985 Sep;28(9):704-7. doi: 10.1007/BF00291980.

Glucagon-like peptide-1 and glucagon-like peptide-2 are encoded by the m-RNA of pancreatic preproglucagon. They show high conservation in different species and substantial sequence homology to glucagon. Because no definite biological activity of these peptides has been reported, we investigated the effect of synthetic C-terminally amidated glucagon-like peptide-1 [1-36] and synthetic human glucagon-like peptide-2 [1-34] with a free C-terminus on insulin release from isolated precultured rat pancreatic islets in the presence of glucose. Glucagon-like peptide-1 stimulates insulin release at 10 and 16.7 mmol/l glucose in a dose-dependent manner. Significant stimulation starts at 2.5 nmol/l in the presence of 10 mmol/l glucose and near maximal release is observed at 250 nmol/l, with approximately 100% increase over basal at both glucose concentrations. The peptide reaches 63% of the maximal stimulatory effect of glucagon. No stimulation occurs in the presence of 2.8 mmol/l glucose. Glucagon-like peptide-2 has no effect on insulin secretion at any glucose concentration tested. It is concluded that glucagon-like peptide-1, in contrast to glucagon-like peptide-2, exhibits a glucose-dependent insulinotropic action on isolated rat pancreatic islets similar to that of glucagon and gastric inhibitory polypeptide.

2. Potential new drug targets for osteoporosis

Chad Deal Nat Clin Pract Rheumatol . 2009 Jan;5(1):20-7. doi: 10.1038/ncprheum0977.

Osteoporosis is a worldwide health problem with a high prevalence. Agents for the treatment of osteoporosis are classified as either antiresorptive or anabolic. Antiresorptive agents work by inhibiting the activity of osteoclasts and, therefore, reducing bone resorption. Currently available antiresorptive agents include bisphosphonates, selective estrogen-receptor modulators, calcitonin and estrogen. Various novel antiresorptive agents are in development. Receptor activator of nuclear factor kappa B ligand is an important cytokine involved in osteoclast activation; denosumab, a fully human monoclonal antibody to this molecule, has finished a major fracture trial. Assessment is underway of odanacatib--an inhibitor of cathepsin K, which is an osteoclast enzyme required for resorption of bone matrix. Glucagon-like peptide 2 is being evaluated for the prevention of the nocturnal rise in bone resorption without affecting bone formation. Anabolic agents act by stimulating formation of new bone. The only anabolic agent currently available in the US is teriparatide--recombinant human parathyroid hormone (PTH)(1-34)--and recombinant human PTH(1-84) is available in Europe. PTH stimulates osteoblast function and bone formation. Novel anabolic agents in development include: antibodies such as sclerostin and dickkopf-1 that target molecules involved in Wnt signaling, a pathway that regulates gene transcription of proteins that are important for osteoblast function; an antagonist to the calcium-sensing receptor; and an activin receptor fusion protein, which functions as an activin antagonist and has shown promise as an anabolic agent in early human trials.