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Merck

G8147

Glucagon-Like Peptide I Amide Fragment 7-36 human

≥97% (HPLC), powder

Synonym(s):

Preproglucagon 78-107 Amide

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About This Item

Empirical Formula (Hill Notation):
C149H226N40O45
CAS Number:
107444-51-9
Molecular Weight:
3297.63
NACRES:
NA.32
PubChem Substance ID:
329799974
UNSPSC Code:
51111800
MDL number:
MFCD00133373

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InChI

1S/C149H226N40O45/c1-17-76(10)119(146(232)167-80(14)126(212)175-104(60-86-63-159-91-36-25-24-35-89(86)91)136(222)177-100(56-73(4)5)137(223)186-117(74(6)7)144(230)174-93(37-26-28-52-150)128(214)160-65-110(197)168-92(122(154)208)39-30-54-158-149(155)156)188-138(224)102(57-83-31-20-18-21-32-83)178-133(219)98(47-51-115(204)205)173-132(218)94(38-27-29-53-151)170-124(210)78(12)164-123(209)77(11)166-131(217)97(44-48-109(153)196)169-111(198)66-161-130(216)96(46-50-114(202)203)172-134(220)99(55-72(2)3)176-135(221)101(59-85-40-42-88(195)43-41-85)179-141(227)106(68-190)182-143(229)108(70-192)183-145(231)118(75(8)9)187-140(226)105(62-116(206)207)180-142(228)107(69-191)184-148(234)121(82(16)194)189-139(225)103(58-84-33-22-19-23-34-84)181-147(233)120(81(15)193)185-112(199)67-162-129(215)95(45-49-113(200)201)171-125(211)79(13)165-127(213)90(152)61-87-64-157-71-163-87/h18-25,31-36,40-43,63-64,71-82,90,92-108,117-121,159,190-195H,17,26-30,37-39,44-62,65-70,150-152H2,1-16H3,(H2,153,196)(H2,154,208)(H,157,163)(H,160,214)(H,161,216)(H,162,215)(H,164,209)(H,165,213)(H,166,217)(H,167,232)(H,168,197)(H,169,198)(H,170,210)(H,171,211)(H,172,220)(H,173,218)(H,174,230)(H,175,212)(H,176,221)(H,177,222)(H,178,219)(H,179,227)(H,180,228)(H,181,233)(H,182,229)(H,183,231)(H,184,234)(H,185,199)(H,186,223)(H,187,226)(H,188,224)(H,189,225)(H,200,201)(H,202,203)(H,204,205)(H,206,207)(H4,155,156,158)/t76-,77-,78-,79-,80-,81+,82+,90-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,117-,118-,119-,120-,121-/m0/s1

SMILES string

CC[C@H](C)[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)Cc4c[nH]cn4)[C@@H](C)O)[C@@H](C)O)C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc5c[nH]c6ccccc56)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O

InChI key

DTHNMHAUYICORS-KTKZVXAJSA-N

assay

≥97% (HPLC)

form

powder

UniProt accession no.

P01275

storage temp.

−20°C

Quality Level

200

Gene Information

human ... GCG(2641)

General description

Glucagon-like peptide 1 (GLP-1) peptide is obtained from proglucagon and is metabolically inactive. However, it is processed to two smaller amide forms, namely GLP-1 (7-37) amide and GLP-1 (7-36) amide. It is a natural gastrointestinal peptide.

Application

Glucagon-Like Peptide (GLP) I Amide Fragment 7-36 human has been used as a GLP-1 receptor agonist:
  • in lysate transfer cyclic adenosine monophosphate (cAMP) assay to test its effect on adenylyl cyclase activity
  • to pre-treat the human umbilical vein endothelial cells (HUVECs) to monitor its effect on hyperpermeability in endothelial cell (EC) monolayers and changes with the actin cytoskeleton
  • to test its inhibitory effect on vascular endothelial growth factor-A (VEGFA) based vasodilation in rat mesenteric arteries

Glucagon-Like Peptide I Amide Fragment 7-36 human has been used as a supplement in DMEM (Dulbeccos′) medium for the culture of 3T3-L1 adipocytes to study the relation between adipose tissue GLP-1 Receptor and obesity and insulin resistance.

Biochem/physiol Actions

GLP-1 (glucagon-like peptide 1) (7-36) amide is a potent insulinotropic peptide, which initiates the glucose-induced insulin release after meals or oral glucose intake. It has an anti-diabetogenic effect and thus, might have use in the treatment of non-insulin dependent diabetes mellitus.

Other Notes

Lyophilized from 0.1% TFA in H2O

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000430572
0000430572
0000294796
0000294797
0000294797

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A Vella et al.
Diabetologia, 45(10), 1410-1415 (2002-10-16)
The aim of this study was to determine whether rapid conversion to inactive and potentially antagonistic peptides could alter the response to GLP-1. We evaluated the ability of exendin-4, a GLP-1 analogue resistant to degradation by dipeptidyl peptidase IV, to
Kinetic analysis of enzymatic and nonenzymatic degradation of peptides by MALDI-TOFMS.
F Rosche et al.
Methods in molecular biology (Clifton, N.J.), 146, 251-272 (2000-08-19)
Song-Tao Tang et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 113, 108667-108667 (2019-03-11)
Glucagon-like peptide-1 (GLP-1) showed protective effects on endothelium-dependent dilatation. Since endothelial barrier dysfunction also plays a pivotal role in atherosclerosis, this study was designed to investigate the effects of GLP-1 on endothelial barrier function in diabetic aortic endothelium and explore
W Creutzfeldt
Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association, 109 Suppl 2, S288-S303 (2001-07-20)
The search for intestinal factors regulating the endocrine secretion of the pancreas started soon after the discovery of secretin, i.e. nearly 100 years ago. Insulinotropic factors of the gut released by nutrients and stimulating insulin secretion in physiological concentrations in
Raik Wolf et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 803(1), 91-99 (2004-03-18)
The incretins, glucose-dependent insulinotropic peptide (GIP(1-42)) and glucagon-like peptide 1 (GLP-1(7-36)), are involved in regulation of gastric emptying, glucose homeostasis, body fat regulation and the glucose-induced insulin secretion from the endocrine pancreas. After release in the circulation both peptides are
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