leucine-2-alanine enkephalin

ロイシン-2-アラニンエンケファリン

WordNet

1. a white crystalline amino acid occurring in proteins that is essential for nutrition; obtained by the hydrolysis of most dietary proteins
2. a crystalline amino acid that occurs in many proteins
3. an endorphin having opiate qualities that occurs in the brain and spinal cord and elsewhere

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/12/17 07:44:08」(JST)

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DADLE
IUPAC name (2R)-2-[[(2S)-2-[[2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
Other names • [D-Ala2, D-Leu5]-Enkephalin • L-Tyrosyl-D-alanylglycyl-L-phenylalanyl-D-Leucine • N-(N-(N-(N-L-tyrosyl-D-alanyl)glycyl)-L-phenylalanyl)-D-Leucine • Tyr-D-Ala-Gly-Phe-D-Leu-OH
Identifiers
CAS number	63631-40-3
PubChem	6917707
ChemSpider	5292936
Jmol-3D images	Image 1
SMILES N[C@H](C(N[C@H](C)C(NCC(N[C@@H](CC1=CC=CC=C1)C(N[C@H](CC(C)C)C(O)=O)=O)=O)=O)=O)CC2=CC=C(O)C=C2
InChI InChI=1S/C29H39N5O7/c1-17(2)13-24(29(40)41)34-28(39)23(15-19-7-5-4-6-8-19)33-25(36)16-31-26(37)18(3)32-27(38)22(30)14-20-9-11-21(35)12-10-20/h4-12,17-18,22-24,35H,13-16,30H2,1-3H3,(H,31,37)(H,32,38)(H,33,36)(H,34,39)(H,40,41)/t18-,22+,23+,24-/m1/s1 Key: ZHUJMSMQIPIPTF-IBURTVSXSA-N InChI=1/C29H39N5O7/c1-17(2)13-24(29(40)41)34-28(39)23(15-19-7-5-4-6-8-19)33-25(36)16-31-26(37)18(3)32-27(38)22(30)14-20-9-11-21(35)12-10-20/h4-12,17-18,22-24,35H,13-16,30H2,1-3H3,(H,31,37)(H,32,38)(H,33,36)(H,34,39)(H,40,41)/t18-,22+,23+,24-/m1/s1 Key: ZHUJMSMQIPIPTF-IBURTVSXBS
Properties
Molecular formula	C29H39N5O7
Molar mass	569.65 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

DADLE ([D-Ala², D-Leu⁵]-Enkephalin) is a synthetic opioid peptide with analgesic properties. Although it is often considered a selective delta opioid receptor agonist, it also binds to the μ₁ subtype of mu opioid receptors.

Treatment with DADLE results in transient depression of mean arterial blood pressure and heart rate.

Its peptide sequence is Tyr-D-Ala-Gly-Phe-D-Leu.

References

UpToDate Contents

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• 1. 胆汁うっ滞系酵素の測定（アルカリホスファターゼ、5' -ヌクレオチダーゼ、γ-グルタミルトランスペプチダーゼなど） enzymatic measures of cholestasis eg alkaline phosphatase 5 nucleotidase gamma glutamyl transpeptidase
• 2. アルコール性肝炎：臨床症状および診断 alcoholic hepatitis clinical manifestations and diagnosis
• 3. ビタミンＫとγカルボキシグルタミン酸の合成および機能 vitamin k and the synthesis and function of gamma carboxyglutamic acid
• 4. 尿素サイクル障害：臨床的特徴および診断 urea cycle disorders clinical features and diagnosis
• 5. 乳児および小児における低血糖に対するアプローチ approach to hypoglycemia in infants and children

English Journal

• Factors that restrict the cell permeation of cyclic prodrugs of an opioid peptide, part 3: Synthesis of analogs designed to have improved stability to oxidative metabolism.

• Nofsinger R, Fuchs-Knotts T, Borchardt RT.SourceDepartment of Pharmaceutical Chemistry, The University of Kansas, Lawrence, Kansas 66047, USA. Rebecca_Nofsinger@Merck.com
• Journal of pharmaceutical sciences.J Pharm Sci.2012 Sep;101(9):3486-99. doi: 10.1002/jps.23109. Epub 2012 Mar 12.
• Previously, our laboratory reported that cyclic peptide prodrugs of the opioid peptide H-Tyr-D-Ala-Gly-Phe-D-Leu-OH (DADLE) are metabolized by cytochrome P450 (CYP450) enzymes, which limits their systemic exposure after oral dosing to animals. In an attempt to design more metabolically stable cyclic
• PMID 22411763

• Factors that restrict the cell permeation of cyclic prodrugs of an opioid peptide, part 4: Characterization of the biopharmaceutical and physicochemical properties of two new cyclic prodrugs designed to be stable to oxidative metabolism by cytochrome P-450 enzymes in the intestinal mucosa.

• Nofsinger R, Borchardt RT.SourceDepartment of Pharmaceutical Chemistry, The University of Kansas, Lawrence, Kansas 66047, USA. Rebecca_Nofsinger@Merck.com
• Journal of pharmaceutical sciences.J Pharm Sci.2012 Sep;101(9):3500-10. doi: 10.1002/jps.23079. Epub 2012 Feb 15.
• The biopharmaceutical and physicochemical properties of two new cyclic prodrugs (CA-[cychexalanine (Cha(4)), D-Leu(5) ]-Enkephalin (Enk) and coumarinic acid (CA)-[Cha(4), D-Ala(5)]-Enk) of opioid peptides that were designed to be stable to oxidative metabolism by cytochrome P-450 enzymes in the inte
• PMID 22337204

• Role of connexin-43 in protective PI3K-Akt-GSK-3β signaling in cardiomyocytes.

• Ishikawa S, Kuno A, Tanno M, Miki T, Kouzu H, Itoh T, Sato T, Sunaga D, Murase H, Miura T.SourceDivision of Cardiology, Second Department of Internal Medicine, Sapporo Medical University, School of Medicine, Sapporo, Japan.
• American journal of physiology. Heart and circulatory physiology.Am J Physiol Heart Circ Physiol.2012 Jun 15;302(12):H2536-44. doi: 10.1152/ajpheart.00940.2011. Epub 2012 Apr 13.
• Sarcolemmal connexin-43 (Cx43) and mitochondrial Cx43 play distinct roles: formation of gap junctions and production of reactive oxygen species (ROS) for redox signaling. In this study, we examined the hypothesis that Cx43 contributes to activation of a major cytoprotective signal pathway, phosphoin
• PMID 22505645

Related Links

• Enkephalin, Leucine-2-Alanine - PubChem - The PubChem ...

Structure, classification, information, physical and chemical properties for 2-Alanyl-leucine enkephalin; Leucine enkephalin-2-alanine; Enkephalin-leu,ala(2); 5-Leucine-2-alanine enkephalin; Tyr-D-Ala-Gly-Phe-Leu

• Leucine-2-alanine enkephalin | Online references ...

DADLE ([D-Ala 2, D-Leu 5]-Enkephalin) is a synthetic opioid peptide with analgesic properties. Although it is often considered a selective delta opioid receptor agonist, it also binds to the μ 1 subtype of mu opioid receptors. Treatment ...

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リンク元	「ロイシン-2-アラニンエンケファリン」
関連記事	「alanine」

「ロイシン-2-アラニンエンケファリン」

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英

leucine-2-alanine enkephalin

「alanine」

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アラニン

関

A、Ala、alanyl、L-alanine