[Asn1,Val5]-Angiotensin II

Angiotensin amide is the octapeptide amide of bovine angiotensin II used to increase blood pressure by vasoconstriction.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
[Asn1,Val5]-Angiotensin II(CAS 53-73-6)

CAT No: 10-101-309

CAS No:53-73-6

Synonyms/Alias:Angiotensin amide;ANGIOTENSINAMIDE;53-73-6;Hypertensine;Ipertensina;Hypertensinamide;Angio tensinamida;Angiotensin II-amide;angiotensinamida;UNII-7WAL1X78KV;Angiotensin (Ciba) (VAN);Val-5-angiotensin II amide;Rainbow trout angiotensin II;5-Valyl-angiotensin II amide;Angiotensin amide [USAN:NF];5-Valine angiotensin II amide;5-Valine-angiotensin amide II;Angiotensin II amide 5-valine;Angiotensin II-5-valine amide;Angiotensinamidum [INN-Latin];Angiotensin amide, 5-L-valine-;Angio tensinamida [INN-Spanish];5-L-Valine-angiotensin II amide;Angiotensinamide [INN];5-Valine-angiotensin II-beta-amide;Angiotensin II, 1-L-asparagine-5-L-valine-;Angiotensin II amide, 5-L-valine-;EINECS 200-182-3;1-Asparagine-5-valine-angiotensin II;1-Asparaginyl-5-valyl-angiotensin II;NSC 107678;(Asn1,Val5)-Angiotensin II;(1-Asparagine-5-valine)-angiotensin II;1-L-Asparagine-5-L-valineangiotensin II;5-Valine-angiotensin II aspartic-beta-amide;Asn-Arg-Val-Tyr-Val-His-Pro-Phe;1-Asparatic acid-5-valine-angiotensin II amide;Angiotensin II aspartic-beta-amide, 5-L-valine;DTXSID401018923;1-Aspartic acid-beta-amide 5-valine-angiotensin II;NSC-107678;Angiotensinamide (INN);MFCD00167643;L-Asparaginyl-L-arginyl-L-valyl-L-tyrosyl-L-valyl-L-histidyl-L-prolyl-L-phenylalanin;(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,4-diamino-4-oxobutanoyl]amino]pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid;L-Phenylalanine, N-(1-(N-(N-(N-(N-(N2-L-asparaginyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-valyl)-L-histidyl)-L-prolyl)-;Angiotensinamidum (INN-Latin);ANGIOTENSINAMIDE (MART.);ANGIOTENSINAMIDE [MART.];Angio tensinamida (INN-Spanish);Angiotensin (Ciba);Angiotensinamidum;L-asparaginyl-L-arginyl-L-valyl-L-tyrosyl-L-valyl-L-histidyl-L-prolyl-L-phenylalanine;Amide, Angiotensin;Angiotensin amide (USAN);ANGIOTENSIN AMIDE [USAN];angiotensine;5 Valine Angiotensin II Amide;5-Valine-Angiotensin II Amide;NSC107678;Amide, 5-Valine-Angiotensin II;(2S)-2-(((2S)-1-((2S)-2-(((2S)-2-(((2S)-2-(((2S)-2-(((2S)-5-(diaminomethylideneamino)-2-(((2S)-2,4-diamino-4-oxobutanoyl)amino)pentanoyl)amino)-3-methylbutanoyl)amino)-3-(4-hydroxyphenyl)propanoyl)amino)-3-methylbutanoyl)amino)-3-(1H-imidazol-5-yl)propanoyl)pyrrolidine-2-carbonyl)amino)-3-phenylpropanoic acid;1 Asparagine 5 valine Angiotensin II;1-Asparagine-5-valine Angiotensin II;Angiotensin II, 1-Asparagine-5-valine;H-Asn-Arg-Val-Tyr-Val-His-Pro-Phe-OH;SCHEMBL9324;7WAL1X78KV;ANGIOTENSIN AMIDE [MI];CHEMBL409803;ANGIOTENSINAMIDE [WHO-DD];C01CX06;CHEBI:135950;JYPVVOOBQVVUQV-CGHBYZBKSA-N;DTXCID601476937;HY-P2212;BDBM50228199;DB13517;DA-48713;FA109691;N-(1-(N-(N-(N-(N-(N(sup 2)-L-Asparaginyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-valyl)-L-histidyl)-L-prolyl)-3-phenyl-L-alanine;CS-0113476;NS00041168;[Asn1, Val5]-Angiotensin II, >=97% (HPLC);Q4763296;(Asn1,Val5)-Angiotensin II (H-Asn-Arg-Val-Tyr-Val-His-Pro-Phe-OH);N-(1-(N-(N-(N-(N-(N2-L-ASPARAGINYL-L-ARGINYL)-L-VALYL)-L-TYROSYL)-L-VALYL)-L-HISTIDYL)-L-PROLYL)-3-PHENYL-L-ALANINE;

Chemical Name:(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-2,4-diamino-4-oxobutanoyl]amino]pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid

Custom Peptide Synthesis
cGMP Peptide
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M.F/Formula
C49H70N14O11
M.W/Mr.
1031.2
Sequence
One Letter Code:NRVYVHPF
Three Letter Code:H-Asn-Arg-Val-Tyr-Val-His-Pro-Phe-OH
Appearance
White or off-white lyophilized powder
Purity
>98%

[Asn1,Val5]-Angiotensin II is a synthetic peptide analogue of the natural octapeptide hormone angiotensin II, distinguished by specific amino acid substitutions at the first and fifth positions—namely, asparagine replacing aspartic acid at position 1 and valine replacing isoleucine at position 5. These targeted modifications confer altered receptor binding affinities and functional properties, making the compound a valuable tool for dissecting the structure-activity relationships within the renin-angiotensin system. As a research-use peptide, [Asn1,Val5]-Angiotensin II is widely utilized in biochemical and pharmacological studies focused on cardiovascular regulation, peptide-receptor interactions, and downstream cellular signaling processes.

Receptor Binding Studies: The analogue is frequently employed to investigate the selectivity and affinity of angiotensin II receptors, particularly the AT1 and AT2 subtypes. By comparing its binding characteristics to those of native angiotensin II, researchers can elucidate the influence of specific side chain modifications on ligand-receptor interactions. These studies are instrumental in mapping critical contact points within the receptor binding pocket and in understanding how subtle changes in peptide structure can impact biological activity.

Signal Transduction Research: [Asn1,Val5]-Angiotensin II serves as a valuable probe in experiments designed to characterize intracellular signaling cascades initiated by angiotensin II receptor activation. By monitoring downstream events such as calcium mobilization, phospholipase C activation, or MAP kinase pathway engagement, investigators can assess how structural modifications in the peptide influence the efficacy and potency of signal transduction. Such insights are integral to advancing the field of G protein-coupled receptor pharmacology.

Peptide Structure-Activity Relationship (SAR) Analysis: The compound is an essential component in SAR studies aiming to delineate the relationship between angiotensin II's primary sequence and its biological effects. Systematic evaluation of analogues like [Asn1,Val5]-Angiotensin II enables researchers to pinpoint residues critical for receptor activation versus those involved in maintaining peptide stability or selectivity. These findings contribute to the rational design of novel peptides with tailored pharmacodynamic properties.

Vascular Physiology Investigations: In ex vivo and in vitro models, [Asn1,Val5]-Angiotensin II is used to examine its effects on vascular smooth muscle contractility and endothelial function. By comparing its activity profile to that of the native peptide, scientists can uncover mechanistic details regarding vasoconstriction, vasodilation, and the modulation of vascular tone. This application supports a deeper understanding of the molecular underpinnings of blood pressure regulation and cardiovascular homeostasis.

Peptide Receptor Antagonist Development: The unique binding and activation profile of [Asn1,Val5]-Angiotensin II makes it a useful reference compound in the screening and development of receptor antagonists or biased agonists. By serving as a functional comparator, it helps researchers evaluate the efficacy and selectivity of novel compounds targeting the angiotensin II receptor pathway. This approach accelerates the identification of new molecular entities for research into receptor modulation and signaling bias.

Source#
Synthetic
Long-term Storage Conditions
Soluble in DMSO
Shipping Condition
RT, or blue ice upon request.
InChI
InChI=1S/C49H70N14O11/c1-26(2)39(61-42(67)33(12-8-18-55-49(52)53)57-41(66)32(50)23-38(51)65)45(70)58-34(20-29-14-16-31(64)17-15-29)43(68)62-40(27(3)4)46(71)59-35(22-30-24-54-25-56-30)47(72)63-19-9-13-37(63)44(69)60-36(48(73)74)21-28-10-6-5-7-11-28/h5-7,10-11,14-17,24-27,32-37,39-40,64H,8-9,12-13,18-23,50H2,1-4H3,(H2,51,65)(H,54,56)(H,57,66)(H,58,70)(H,59,71)(H,60,69)(H,61,67)(H,62,68)(H,73,74)(H4,52,53,55)/t32-,33-,34-,35-,36-,37-,39-,40-/m0/s1
InChI Key
JYPVVOOBQVVUQV-CGHBYZBKSA-N
Canonical SMILES
CC(C)C(C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(C(C)C)C(=O)NC(CC2=CN=CN2)C(=O)N3CCCC3C(=O)NC(CC4=CC=CC=C4)C(=O)O)NC(=O)C(CCCN=C(N)N)NC(=O)C(CC(=O)N)N
Isomeric SMILES
CC(C)[C@@H](C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC2=CN=CN2)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(=O)N)N

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