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G2044

Sigma-Aldrich

Glucagon

synthetic, powder, suitable for cell culture

Synonym(s):

GlucaGen, Glucagon peptide

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About This Item

Empirical Formula (Hill Notation):
C153H225N43O49S
CAS Number:
Molecular Weight:
3482.75
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

assay

≥95% (HPLC)

form

powder

potency

0.3-10 μg/mL

technique(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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Structure-conformation-activity studies of glucagon and semi-synthetic glucagon analogs
Hruby VJ
Molecular and Cellular Biochemistry, 44(1), 49-64 (1982)
Problem or solution: The strange story of glucagon
Scott RV and Bloom SR
Peptides, 100, 36-41 (2018)

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