G2044

Sigma-Aldrich

Glucagon

synthetic, powder, suitable for cell culture

Empirical Formula (Hill Notation):
C153H225N43O49S
CAS Number:
Molecular Weight:
3482.75
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic

assay

≥95% (HPLC)

form

powder

potency

0.3-10 μg/mL

application(s)

cell culture | mammalian: suitable

solubility

0.05 M acetic acid: 1 mg/mL, clear, colorless

shipped in

wet ice

storage temp.

2-8°C

SMILES string

Cl[H].[H]N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](C(C)O)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](C(C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](Cc3ccc(O)cc3)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc4ccc(O)cc4)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](Cc5ccccc5)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc6c[nH]c7ccccc67)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)O)C(O)=O

InChI

1S/C153H225N43O49S.ClH/c1-72(2)52-97(133(226)176-96(47-51-246-11)132(225)184-104(60-115(159)209)143(236)196-123(78(10)203)151(244)245)179-137(230)103(58-83-64-167-89-29-19-18-28-87(83)89)183-131(224)95(43-46-114(158)208)177-148(241)120(74(5)6)194-141(234)101(54-79-24-14-12-15-25-79)182-138(231)105(61-117(211)212)185-130(223)94(42-45-113(157)207)171-124(217)75(7)170-127(220)91(31-22-49-165-152(160)161)172-128(221)92(32-23-50-166-153(162)163)174-146(239)110(69-199)191-140(233)107(63-119(215)216)186-134(227)98(53-73(3)4)178-135(228)99(56-81-33-37-85(204)38-34-81)180-129(222)90(30-20-21-48-154)173-145(238)109(68-198)190-136(229)100(57-82-35-39-86(205)40-36-82)181-139(232)106(62-118(213)214)187-147(240)111(70-200)192-150(243)122(77(9)202)195-142(235)102(55-80-26-16-13-17-27-80)188-149(242)121(76(8)201)193-116(210)66-168-126(219)93(41-44-112(156)206)175-144(237)108(67-197)189-125(218)88(155)59-84-65-164-71-169-84;/h12-19,24-29,33-40,64-65,71-78,88,90-111,120-123,167,197-205H,20-23,30-32,41-63,66-70,154-155H2,1-11H3,(H2,156,206)(H2,157,207)(H2,158,208)(H2,159,209)(H,164,169)(H,168,219)(H,170,220)(H,171,217)(H,172,221)(H,173,238)(H,174,239)(H,175,237)(H,176,226)(H,177,241)(H,178,228)(H,179,230)(H,180,222)(H,181,232)(H,182,231)(H,183,224)(H,184,225)(H,185,223)(H,186,227)(H,187,240)(H,188,242)(H,189,218)(H,190,229)(H,191,233)(H,192,243)(H,193,210)(H,194,234)(H,195,235)(H,196,236)(H,211,212)(H,213,214)(H,215,216)(H,244,245)(H4,160,161,165)(H4,162,163,166);1H/t75-,76+,77+,78+,88-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,120-,121-,122-,123-;/m0./s1

InChI key

RKGLLHCSSVJTAN-YYICOITRSA-N

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Amino Acid Sequence

His-Ser-Gln-Gly-Thr-Phe-Thr-Ser-Asp-Tyr-Ser-Lys-Tyr-Leu-Asp-Ser-Arg-Arg-Ala-Gln-Asp-Phe-Val-Gln-Trp-Leu-Met-Asn-Thr

General description

Glucagon is a peptide hormone of 29 amino acids secreted by alpha cells in the pancreas. Its release is controlled by hypothalamus when glucose levels in the blood decreases. The C-terminal region of glucagon is crucial for receptor binding.

Application

Glucagon has been used:
  • in the stimulation of human primary hepatocytes for cyclic adenosine monophosphate (cAMP) production
  • for measuring glucagon response in mice
  • to induce gluconeogenic stimuli in primary hepatocytes

Packaging

1, 5, 25 mg in glass bottle

Biochem/physiol Actions

Glucagon functions to elevate glucose by activating GCGR in liver mediating the glucose circulation in blood. The hyperglucagonemia elevated levels of glucagon is observed in diabetes and in nonalcoholic fatty liver disease, post gastric bypass surgery and glucagon based tumors.

Components

H-His-Ser-Gln-Gly-Thr-Phe-Thr-Ser-Asp-Tyr-Ser-Lys-Tyr-Leu-Asp-Ser-Arg-Arg-Ala-Gln-Asp-Phe-Val-Gln-Trp-Leu-Met-Asn-Thr-OH.xHCl

Other Notes

This product is a chemically synthesized glucagon qualified for use in cell culture applications.

Physical form

powder-0 °C; stock-frozen in working aliquots, avoid repeated freeze/thaw

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Structure-conformation-activity studies of glucagon and semi-synthetic glucagon analogs
Hruby VJ
Molecular and Cellular Biochemistry, 44(1), 49-64 (1982)
Fatty acids-stress attenuates gluconeogenesis induction and glucose production in primary hepatocytes
Budick-Harmelin N, et al.
Lipids in Health and Disease, 11(1), 66-66 (2012)
Problem or solution: The strange story of glucagon
Scott RV and Bloom SR
Peptides, 100, 36-41 (2018)
Lipodystrophy due to adipose tissue-specific insulin receptor knockout results in progressive NAFLD
Softic S, et al.
Diabetes, 65(8), 2187-2200 (2016)
Camille Huet et al.
The Journal of biological chemistry, 295(18), 5836-5849 (2020-03-19)
The cellular energy sensor AMP-activated protein kinase (AMPK) is a metabolic regulator that mediates adaptation to nutritional variations to maintain a proper energy balance in cells. We show here that suckling-weaning and fasting-refeeding transitions in rodents are associated with changes...
Articles
Glucose metabolism is regulated by the opposing actions of insulin and glucagon. Insulin is released from pancreatic ß cells in response to high blood glucose levels and regulates glucose metabolism through its actions on muscle, liver, and adipose tissue.
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