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GLP-2 (1-33) (human)

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

GLP-2 (human) is an endogenous peptide that acts as an intestinal epithelium-specific growth factor. It stimulates cell proliferation and inhibits apoptosis, and also modulates intestinal glucose transport, food intake, and gastric acid secretion.

Category

Peptide Inhibitors

Catalog number

BAT-010178

CAS number

223460-79-5

Molecular Formula

C165H254N44O55S

Molecular Weight

3766.1

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S,3R)-2-[[(2S,3S)-2-[[(2S)-6-amino-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S,3R)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]propanoyl]amino]-3-carboxypropanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-4-carboxybutanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxybutanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-carboxypropanoyl]amino]-4-oxobutanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-3-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]butanedioic acid

Synonyms

Glucagon-like peptide 2 (human); GLP-2 (human); GLP 2 (human)

Purity

>98%

Sequence

HADGSFSDEMNTILDNLAARDFINWLIQTKITD

Storage

Store at -20°C

InChI

InChI=1S/C165H254N44O55S/c1-22-77(11)126(157(256)187-96(45-47-115(168)215)142(241)207-130(84(18)212)161(260)186-94(43-34-35-50-166)141(240)203-129(80(14)25-4)160(259)209-131(85(19)213)162(261)201-112(164(263)264)67-125(230)231)204-152(251)101(55-76(9)10)190-146(245)104(58-89-68-176-93-42-33-32-41-91(89)93)193-148(247)106(61-117(170)217)200-158(257)127(78(12)23-2)205-153(252)103(57-88-39-30-27-31-40-88)191-150(249)110(65-123(226)227)196-138(237)95(44-36-51-175-165(172)173)183-134(233)82(16)179-133(232)81(15)181-143(242)99(53-74(5)6)189-147(246)105(60-116(169)216)195-151(250)111(66-124(228)229)197-144(243)100(54-75(7)8)199-159(258)128(79(13)24-3)206-163(262)132(86(20)214)208-154(253)107(62-118(171)218)194-140(239)98(49-52-265-21)185-139(238)97(46-48-120(220)221)184-149(248)109(64-122(224)225)198-156(255)114(72-211)202-145(244)102(56-87-37-28-26-29-38-87)192-155(254)113(71-210)182-119(219)70-177-137(236)108(63-121(222)223)188-135(234)83(17)180-136(235)92(167)59-90-69-174-73-178-90/h26-33,37-42,68-69,73-86,92,94-114,126-132,176,210-214H,22-25,34-36,43-67,70-72,166-167H2,1-21H3,(H2,168,215)(H2,169,216)(H2,170,217)(H2,171,218)(H,174,178)(H,177,236)(H,179,232)(H,180,235)(H,181,242)(H,182,219)(H,183,233)(H,184,248)(H,185,238)(H,186,260)(H,187,256)(H,188,234)(H,189,246)(H,190,245)(H,191,249)(H,192,254)(H,193,247)(H,194,239)(H,195,250)(H,196,237)(H,197,243)(H,198,255)(H,199,258)(H,200,257)(H,201,261)(H,202,244)(H,203,240)(H,204,251)(H,205,252)(H,206,262)(H,207,241)(H,208,253)(H,209,259)(H,220,221)(H,222,223)(H,224,225)(H,226,227)(H,228,229)(H,230,231)(H,263,264)(H4,172,173,175)/t77-,78-,79-,80-,81-,82-,83-,84+,85+,86+,92-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,126-,127-,128-,129-,130-,131-,132-/m0/s1

InChI Key

TWSALRJGPBVBQU-PKQQPRCHSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(C(C)O)C(=O)NC(CC(=O)O)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=CNC=N5)N

1.GLP-2 has differential effects on small intestine growth and function in fetal and neonatal pigs.

Petersen YM1, Burrin DG, Sangild PT. Am J Physiol Regul Integr Comp Physiol. 2001 Dec;281(6):R1986-93.

Glucagon-like peptide-2 (GLP-2) is a potent intestinotropic factor in neonatal and adult animals. However, the GLP-2 responsiveness of the fetal intestine has not been established. To determine how stage of development affects the responsiveness to GLP-2, we examined GLP-2 receptor (GLP-2R) expression, gut morphology, and brush-border enzyme mRNA and activities in late-gestation fetal (n = 7) and parenterally fed neonatal (n = 7) piglets given GLP-2 (12.5 nmol/kg) twice daily for 6 days. The GLP-2R was expressed in the fetal and neonatal gastrointestinal tract. The biologically active GLP-2-(1-33) was undetectable (<5 pmol/l) in plasma of 98-day-gestation fetuses but increased significantly toward full term (115 days, 11 +/- 1 pmol/l) and in neonates fed by total parenteral nutrition (23 +/- 5 pmol/l). Exogenous GLP-2 had no effect on gut growth in fetuses but increased intestinal weight and villus height in neonates (P < 0.05). Crypt cell proliferation and the enzymes sucrase-isomaltase, lactase-phloridzin hydrolase, aminopeptidase A, and dipeptidyl peptidase IV were unchanged by GLP-2 in both groups.

2.Synthesis and Pharmacological Characterization of Novel Glucagon-like Peptide-2 (GLP-2) Analogues with Low Systemic Clearance.

Wiśniewski K1, Sueiras-Diaz J1, Jiang G1, Galyean R1, Lu M1, Thompson D1, Wang YC1, Croston G1, Posch A1, Hargrove DM1, Wiśniewska H1, Laporte R1, Dwyer JJ1, Qi S1, Srinivasan K1, Hartwig J1, Ferdyan N1, Mares M1, Kraus J1, Alagarsamy S1, Rivière PJ1, Schteingart CD1. J Med Chem. 2016 Apr 14;59(7):3129-39. doi: 10.1021/acs.jmedchem.5b01909. Epub 2016 Mar 25.

Glucagon-like peptide-2 receptor agonists have therapeutic potential for the treatment of intestinal diseases. The native hGLP-2, a 33 amino acid gastrointestinal peptide, is not a suitable clinical candidate, due to its very short half-life in humans. In search of GLP-2 receptor agonists with better pharmacokinetic characteristics, a series of GLP-2 analogues containing Gly substitution at position 2, norleucine in position 10, and hydrophobic substitutions in positions 11 and/or 16 was designed and synthesized. In vitro receptor potency at the human GLP-2, selectivity vs the human GLP-1 and GCG receptors, and PK profile in rats were determined for the new analogues. A number of compounds more potent at the hGLP-2R than the native hormone, showing excellent receptor selectivity and very low systemic clearance (CL) were discovered. Analogues 69 ([Gly(2),Nle(10),d-Thi(11),Phe(16)]hGLP-2-(1-30)-NH2), 72 ([Gly(2),Nle(10),d-Phe(11),Leu(16)]hGLP-2-(1-33)-OH), 73 ([Gly(2),Nle(10),d-Phe(11),Leu(16)]hGLP-2-(1-33)-NH2), 81 ([Gly(2),Nle(10),d-Phe(11),Leu(16)]hGLP-2-(1-33)-NHEt), and 85 ([Gly(2),Nle(10),d-Phe(11),Leu(16)]hGLP-2-(1-33)-NH-((CH2)2O)4-(CH2)2-CONH2) displayed the desired profiles (EC50 (hGLP-2R) < 100 pM, CL in rat <0.

3.Carcinogenic effects of exogenous and endogenous glucagon-like peptide-2 in azoxymethane-treated mice.

Iakoubov R1, Lauffer LM, Trivedi S, Kim YI, Brubaker PL. Endocrinology. 2009 Sep;150(9):4033-43. doi: 10.1210/en.2009-0295. Epub 2009 Jun 4.

Glucagon-like peptide-2 (GLP-2) is a nutrient-dependent intestinotropic hormone that promotes intestinal growth, via increased intestinal proliferation and decreased apoptosis, as well as increases in nutrient absorption and barrier function. The long-acting analog h(Gly(2))GLP-2[1-33] is currently being tested for treatment of short bowel syndrome and Crohn's disease. However, the role of GLP-2 in colon carcinogenesis is controversial. To assess the intestinotropic effects of exogenous and endogenous GLP-2, C57BL6/J mice were injected with 1 microg h(Gly(2))GLP-2[1-33]; 30 or 60 ng hGLP-2[3-33], a GLP-2 receptor antagonist; or PBS (4 wk, twice a day, sc). Chronic h(Gly(2))GLP-2[1-33] increased small intestinal weight/body weight (P < 0.001), villus height (P < 0.001), crypt depth (P < 0.001), and crypt cell proliferation, as measured by expression of the proliferative marker Ki67 (P < 0.05-0.01). In contrast, chronic hGLP-2[3-33] decreased small intestinal weight/body weight (P < 0.

4.Secretion of the intestinotropic hormone glucagon-like peptide 2 is differentially regulated by nutrients in humans.

Xiao Q1, Boushey RP, Drucker DJ, Brubaker PL. Gastroenterology. 1999 Jul;117(1):99-105.

BACKGROUND & AIMS: Glucagon-like peptide 2(1-33) (GLP-2(1-33)), an intestinally derived hormone, stimulates growth in rodent small and large bowel. To explore the physiology of GLP-2(1-33) secretion, we measured plasma GLP-2 levels in 6 healthy male volunteers, before and after test meals.