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Ac-RYYRWK-NH2

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Ac-RYYRWK-NH, a hexapeptide, is a partial agonist of the nociceptin/orphanin FQ (N/OFQ) peptide (NOP) receptorr (Ki = 0.71 nM), which exhibits selectivity over μ, δ and κ opioid receptors (IC50 > 4000 nM).

Category

Peptide Inhibitors

Catalog number

BAT-010805

CAS number

200959-47-3

Molecular Formula

C49H69N15O9

Molecular Weight

1012.17

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-6-aminohexanamide

Synonyms

L-Lysinamide, N2-acetyl-L-arginyl-L-tyrosyl-L-tyrosyl-L-arginyl-L-tryptophyl-; N2-Acetyl-L-arginyl-L-tyrosyl-L-tyrosyl-L-arginyl-L-tryptophyl-L-lysinamide; Ac-Arg-Tyr-Tyr-Arg-Trp-Lys-NH2; N-acetyl-L-arginyl-L-tyrosyl-L-tyrosyl-L-arginyl-L-tryptophyl-L-lysinamide

Related CAS

2863657-54-7 (acetate salt) 408305-09-9 (TFA salt)

Purity

≥95%

Density

1.44±0.1 g/cm3

Sequence

Ac-RYYRWK-NH2

Storage

Store at -20°C

InChI

InChI=1S/C49H69N15O9/c1-28(65)59-37(11-6-22-56-48(52)53)43(69)62-40(25-30-15-19-33(67)20-16-30)46(72)63-39(24-29-13-17-32(66)18-14-29)45(71)61-38(12-7-23-57-49(54)55)44(70)64-41(26-31-27-58-35-9-3-2-8-34(31)35)47(73)60-36(42(51)68)10-4-5-21-50/h2-3,8-9,13-20,27,36-41,58,66-67H,4-7,10-12,21-26,50H2,1H3,(H2,51,68)(H,59,65)(H,60,73)(H,61,71)(H,62,69)(H,63,72)(H,64,70)(H4,52,53,56)(H4,54,55,57)/t36-,37-,38-,39-,40-,41-/m0/s1

InChI Key

YROQVQIJRORFAZ-SKGSPYGFSA-N

Canonical SMILES

CC(=O)NC(CCCN=C(N)N)C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CCCCN)C(=O)N

1.Synthesis and biological activity of novel small peptides with aminophosphonates moiety as NOP receptor ligands.

Naydenova ED;Todorov PT;Mateeva PI;Zamfirova RN;Pavlov ND;Todorov SB Amino Acids. 2010 Nov;39(5):1537-43. doi: 10.1007/s00726-010-0624-1. Epub 2010 May 25.

The aim of the present study was the synthesis and the biological screening of new analogs of Ac-RYYRWK-NH2, modified at the N-terminal with 1-[(methoxyphosphono)methylamino]cycloalkanecarboxylic acids. The four newly synthesized ligands for the nociceptin/orphanin FQ (N/OFQ) receptor (NOP) have been prepared by solid-phase peptide synthesis--Fmoc-strategy. These compounds were tested for agonistic activity in vitro on electrically stimulated smooth-muscle preparations isolated from vas deferens of Wistar rats. Our data showed that substitution of Arg at position 1 with aminophosphonates moiety decreased significantly the affinity of ligands to the NOP receptor. Furthermore, the enlargement of the cycle (with 5-8 carbon atoms) additionally diminished both the activity and the selectivity for NOP-receptor.

2.Synthesis and changes in affinity for NOP and opioid receptors of novel hexapeptides containing β(2)-tryptophan analogues.

Zamfirova R;Pavlov N;Todorov P;Mateeva P;Martinez J;Calmès M;Naydenova E Bioorg Med Chem Lett. 2013 Jul 15;23(14):4052-5. doi: 10.1016/j.bmcl.2013.05.064. Epub 2013 May 28.

We report the synthesis and the biological activity of new analogues of Ac-RFMWMK-NH2 and Ac-RYYRWK-NH2, modified in position 4 and 5, respectively, with incorporation of newly synthesized β(2)-tryptophan analogues. Trp was substituted by the (S)-2-(1-methyl-1H-indol-3-yl)propionic residue or by (S)-2-(5-methoxy-1H-indol-3-yl)propionic residue. The biological activity (pEC50 and Emax) of these compounds was tested on electrically stimulated preparations of rat vas deferens. The 5-methoxy β-tryptophan group reverses the affinity of the compounds.

3.Tryptophan replacement in the nociceptin/orphanin FQ receptor ligand Ac-RYYRWK-NH2.

Carra' G;Calo' G;Spagnolo B;Guerrini R;Arduin M;Marzola E;Trapella C;Regoli D;Salvadori S J Pept Res. 2005 Jul;66(1):39-47.

In the present study we describe the in vitro pharmacological characterization of the nociceptin/orphanin FQ (N/OFQ) receptor (NOP) ligand Ac-RYYRWK-NH2 and the synthesis and biological evaluation of 13 Trp5 substituted Ac-RYYRWK-NH2 analogs. Results indicate that Ac-RYYRWK-NH2 behaves as a highly potent and selective partial agonist at the NOP receptors and that the whole indole moiety of the Trp5 side chain is not required, being a phenyl-ethyl side chain already sufficient for maintaining high potency.