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V6879

Sigma-Aldrich

[Lys8]-Vasopressin

≥98% (HPLC)

Synonym(s):

Lysine vasopressin, Lyspressin

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About This Item

Empirical Formula (Hill Notation):
C46H65N13O12S2
CAS Number:
50-57-7
Molecular Weight:
1056.22
EC Number:
200-050-5
MDL number:
MFCD00133970
UNSPSC Code:
51111800
PubChem Substance ID:
24900764
NACRES:
NA.32

biological source

synthetic (organic)

sterility

non-sterile

Assay

≥98% (HPLC)

form

powder

solubility

0.1 M acetic acid: 20 mg/mL, clear, colorless

UniProt accession no.

P01185

shipped in

ambient

storage temp.

−20°C

SMILES string

CC(O)=O.NCCCCC(NC(=O)C1CCCN1C(=O)C2CSSCC(N)C(=O)NC(Cc3ccc(O)cc3)C(=O)NC(Cc4ccccc4)C(=O)NC(CCC(N)=O)C(=O)NC(CC(N)=O)C(=O)N2)C(=O)NCC(N)=O

InChI

1S/C46H65N13O12S2.C2H4O2/c47-17-5-4-9-29(40(65)52-22-38(51)63)54-45(70)35-10-6-18-59(35)46(71)34-24-73-72-23-28(48)39(64)55-31(20-26-11-13-27(60)14-12-26)43(68)56-32(19-25-7-2-1-3-8-25)42(67)53-30(15-16-36(49)61)41(66)57-33(21-37(50)62)44(69)58-34;1-2(3)4/h1-3,7-8,11-14,28-35,60H,4-6,9-10,15-24,47-48H2,(H2,49,61)(H2,50,62)(H2,51,63)(H,52,65)(H,53,67)(H,54,70)(H,55,64)(H,56,68)(H,57,66)(H,58,69);1H3,(H,3,4)

InChI key

NKWAIKZITYLOMT-UHFFFAOYSA-N

Gene Information

human ... AVP(551)

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Amino Acid Sequence

Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2 [Disulfide Bridge: 1-6]

Application

[Lys8]-Vasopressin was used as a test compound in quantitative analysis of peptides and proteins by using on-line capillary isoelectric focusing-mass spectrometry.The product was used for studying the coupling of a polymer-based microchip electrophoresis to MALDI-TOF MS by using rotating ball interface.

Biochem/physiol Actions

Predominant form of vasopressin present in pigs and marsupials. It has lower vasopressor and antidiuretic activity than Arg8-vasopressin.
[Lys8]-Vasopressin also refers as Lysine vasopressin or Lyspressin is the predominant form of vasopressin present in pigs and marsupials. It antagonizes the amnesia in rats. Lyspressin can also induce resistance to extinction of active avoidance behaviour.

Preparation Note

2 mg of [Lys8]-Vasopressin dissolves in 0.1 mL, 0.1M HOAc to yield a clear, colorless solution.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Binoy Shivanna et al.
The Cochrane database of systematic reviews, 3(3), CD009171-CD009171 (2013-04-02)
Neonatal hypotension that is refractory to volume expansion, catecholamines, or corticosteroids has a mortality of about 50%. Optimization of blood pressure and tissue perfusion in refractory hypotension may be crucial to improve clinical outcomes. Vasopressin, a neuropeptide hormone, or its
V Gorbulev et al.
European journal of biochemistry, 215(1), 1-7 (1993-07-01)
[Arg8]vasopressin and oxytocin are the two main members of the neurohypophysial hormone family found to be present in nearly all mammals. [Lys8]vasopressin ([Lys8]VP) has been identified as the antidiuretic hormone in pig and some marsupial families. The porcine-derived kidney epithelial
D Crankshaw
European journal of pharmacology, 173(2-3), 183-188 (1989-12-07)
The effects of a number of neurohypophyseal hormones and analogues on the contractility of rabbit urinary bladder smooth muscle in vitro were examined. The order of potency was [Arg8]vasopressin = [Lys8]vasotocin greater than [Lys8]vasopressin greater than [Arg8]vasotocin much greater than
Paolo Biban et al.
Current drug metabolism, 14(2), 186-192 (2013-02-27)
Vasopressin and its analogue terlipressin are potent vasopressors which have been recently proposed in the treatment of catecholamine-resistant septic shock. We review the physiology, metabolism and pharmacology of vasopressin and terlipressin, as well as the available data on their efficacy
P A Melrose et al.
Brain, behavior and evolution, 33(4), 193-204 (1989-01-01)
The present study describes the topography of immunoreactive (ir) oxytocin (OXY) and vasopressin (AVP) neurons in the forebrain of Equus caballus and the coexistence of ir proopiomelanocortin (POMC)-derived peptides in the same cells. These data are compared to those for
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