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Merck

C4999

Sigma-Aldrich

Proinsulin C-Peptide (55-89) human

bioactive peptide hormone

Synonym(e):

Proinsulin connecting peptide

Anmeldenzur Ansicht organisationsspezifischer und vertraglich vereinbarter Preise


About This Item

Empirische Formel (Hill-System):
C153H259N49O52
CAS-Nummer:
Molekulargewicht:
3616.99
MDL-Nummer:
UNSPSC-Code:
12352209
PubChem Substanz-ID:
NACRES:
NA.26

Qualitätsniveau

Assay

≥95% (HPLC)

Form

powder

Farbe

white

Lagertemp.

−20°C

SMILES String

CC(C)C[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](N)CCCNC(N)=N)C(C)C)C(C)C)C(=O)NCC(=O)NCC(=O)NCC(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O

InChI

1S/C153H259N49O52/c1-71(2)55-94(193-134(237)91(40-48-119(222)223)189-148(251)122(78(15)16)200-135(238)86(33-41-105(156)205)179-112(212)67-175-147(250)121(77(13)14)199-136(239)88(35-43-107(158)207)188-139(242)97(58-74(7)8)194-142(245)100(61-120(224)225)197-133(236)90(39-47-118(220)221)182-124(227)80(18)177-129(232)89(38-46-117(218)219)186-130(233)84(29-23-51-167-152(162)163)183-126(229)82(155)27-22-50-166-151(160)161)128(231)172-63-110(210)169-62-109(209)170-68-115(215)201-53-25-31-103(201)145(248)174-64-111(211)176-79(17)123(226)171-65-113(213)180-101(69-203)144(247)196-99(60-76(11)12)141(244)190-92(36-44-108(159)208)149(252)202-54-26-32-104(202)146(249)198-95(56-72(3)4)137(240)178-81(19)125(228)192-96(57-73(5)6)138(241)185-85(37-45-116(216)217)127(230)173-66-114(214)181-102(70-204)143(246)195-98(59-75(9)10)140(243)187-87(34-42-106(157)206)132(235)184-83(28-20-21-49-154)131(234)191-93(150(253)254)30-24-52-168-153(164)165/h71-104,121-122,203-204H,20-70,154-155H2,1-19H3,(H2,156,205)(H2,157,206)(H2,158,207)(H2,159,208)(H,169,210)(H,170,209)(H,171,226)(H,172,231)(H,173,230)(H,174,248)(H,175,250)(H,176,211)(H,177,232)(H,178,240)(H,179,212)(H,180,213)(H,181,214)(H,182,227)(H,183,229)(H,184,235)(H,185,241)(H,186,233)(H,187,243)(H,188,242)(H,189,251)(H,190,244)(H,191,234)(H,192,228)(H,193,237)(H,194,245)(H,195,246)(H,196,247)(H,197,236)(H,198,249)(H,199,239)(H,200,238)(H,216,217)(H,218,219)(H,220,221)(H,222,223)(H,224,225)(H,253,254)(H4,160,161,166)(H4,162,163,167)(H4,164,165,168)/t79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,121-,122-/m0/s1

InChIKey

JEPNOJXFZHBCTB-ZCUALFGZSA-N

Amino Acid Sequence

Arg-Arg-Glu-Ala-Glu-Asp-Leu-Gln-Val-Gly-Gln-Val-Glu-Leu-Gly-Gly-Gly-Pro-Gly-Ala-Gly-Ser-Leu-Gln-Pro-Leu-Ala-Leu-Glu-Gly-Ser-Leu-Gln-Lys-Arg

Allgemeine Beschreibung

Human proinsulin, the single-chain peptide precursor of insulin, consists of the insulin A and B chains connected by the 31 amino acid C-peptide. Cleavage of proinsulin by proteolytic enzymes produces insulin and free C-peptide. The product here is the 35-mer peptide (Arg−Arg-C-Peptide-Lys-Arg) observed to separate the insulin A and B chains.

Biochem./physiol. Wirkung

C-Peptide Fragment (55-89) is a fragment derived from the proinsulin C-peptide. C-peptide has cell signaling activity that involves calcium-dependent intracellular signaling. C-Peptide Fragment 55-89 may be used to help researchers understand the role of specific sequences within the C-peptide in binding, conformation and function of C-peptide.
C-Peptide was initially thought to have no intrinsic biological activity. More recent research has identified multiple biological effects of C-peptide, including binding to cell membranes, activation of signaling pathways, and stimulation of Na+,K+-ATPase and endothelial nitric oxide synthetase. However, the exact function of C-peptide is unclear due to conflicting physiological effects.

Sonstige Hinweise

Lyophilized from 0.1% TFA in H2O

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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1 of 2

C-Peptide: A new mediator of atherosclerosis in diabetes.
Vasic, D., and Walcher, D.
Mediators of Inflammation, 858692-858692 (2012)
Proinsulin C-peptide prevents type-1 diabetes-induced decrease of renal Na+-K+-ATPase α1-subunit in rats.
Nordquist L, Shimada K, et al.
Diabetes and Metabolism, 26, 193-199 (2010)
R S Mughal et al.
Diabetologia, 53(8), 1761-1771 (2010-05-13)
Endothelial cells (ECs) and smooth muscle cells (SMCs) play key roles in the development of intimal hyperplasia in saphenous vein (SV) bypass grafts. In diabetic patients, insulin administration controls hyperglycaemia but cardiovascular complications remain. Insulin is synthesised as a pro-peptide
The conformational protential of porcine proinsulin C-peptide.
Vogt HP, Wollmer A, et al.
Hoppe-Seyler'S Zeitschrift fur Physiologische Chemie, 357, 107-116 (1971)
Intracellular signaling by C-peptide.
Hills, C.E. and Brunskill, N.J.
Experimental Diabetes Research, 635158-635158 (2008)

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