Leu-encefalina

Leu-encefalina
	Nome IUPAC ácido (2R)-2-[[(2R)-2-[[2-[[2-[[(2R)-2-amino-3-(4-hidroxifenil)propanoil]amino]acetil]amino]acetil]amino]-3-fenilpropanoil]amino]-4-metilpentanoico
	Outros nomes [Leu]encefalina; [Leu5]encefalina; leu-encefalina; leucina encefalina
Identificadores
Número CAS	58822-25-6
PubChem	461776
ChemSpider	406229
UNII	RI01R707R6
ChEBI	CHEBI:89656
ChEMBL	CHEMBL8234
Ligando IUPHAR	1613
Imaxes 3D Jmol	Image 1
	SMILES O=C(O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)Cc2ccccc2)CC(C)C ;
	InChI InChI=1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1; Key: URLZCHNOLZSCCA-VABKMULXSA-N InChI=1/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1; Key: URLZCHNOLZSCCA-VABKMULXBR;
Propiedades
Fórmula molecular	C28H37N5O7
Masa molecular	555,62 g/mol
	; Se non se indica outra cousa, os datos están tomados en condicións estándar de 25 °C e 100 kPa.

A Leu-encefalina ou leu-encefalina é un péptido opiáceo endóxeno neurotransmisor coa secuencia de aminoácidos Tyr-Gly-Gly-Phe-Leu, que se atopa de forma natural nos cerebros de moitos animais, incluíndo os humanos.^[2]^[3] É unha das dúas formas de encefalina existentes; a outra é a Met-encefalina.^[2] O residuo de tirosina na posición 1 pénsase que é análogo ao grupo 3-hidroxilo da morfina.^[4] A Leu-encefalina ten accións agonistas tanto no receptor opiáceo μ coma no receptor opiáceo δ, cunha preferencia significativamente maior polo último. Non ten efecto sobre o receptor opiáceo κ.^[5]^[6]

Notas

↑ Colaianni L, Kung SC, Taggart DK, Picca RA, Greaves J, Penner RM, Cioffi N (xullo de 2014). "Reduction of spectral interferences using ultraclean gold nanowire arrays in the LDI-MS analysis of a model peptide". Analytical and Bioanalytical Chemistry 406 (19): 4571–83. PMID 24980599. doi:10.1007/s00216-014-7876-7.
↑ ^2,0 ^2,1 Lazarus LH, Ling N, Guillemin R (xuño 1976). "beta-Lipotropin as a prohormone for the morphinomimetic peptides endorphins and enkephalins". Proceedings of the National Academy of Sciences of the United States of America 73 (6): 2156–9. Bibcode:1976PNAS...73.2156L. PMC 430469. PMID 1064883. doi:10.1073/pnas.73.6.2156.
↑ Hughes J, Kosterlitz HW, Smith TW (febreiro de 1997). "The distribution of methionine-enkephalin and leucine-enkephalin in the brain and peripheral tissues. 1977". British Journal of Pharmacology 120 (4 Suppl): 428–36; discussion 426–7. PMC 3224324. PMID 9142421. doi:10.1111/j.1476-5381.1997.tb06829.x.
↑ Schiller PW, Yam CF, Lis M (maio de 1977). "Evidence for topographical analogy between methionine-enkephalin and morphine derivatives". Biochemistry 16 (9): 1831–8. PMID 870028. doi:10.1021/bi00628a011.
↑ Porreca F, Mosberg HI, Hurst R, Hruby VJ, Burks TF (agosto de 1984). "Roles of mu, delta and kappa opioid receptors in spinal and supraspinal mediation of gastrointestinal transit effects and hot-plate analgesia in the mouse". The Journal of Pharmacology and Experimental Therapeutics 230 (2): 341–8. PMID 6086883.
↑ Raynor K, Kong H, Chen Y, Yasuda K, Yu L, Bell GI, Reisine T (febreiro de 1994). "Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors". Molecular Pharmacology 45 (2): 330–4. PMID 8114680.

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[pmid24980599-1] Colaianni L, Kung SC, Taggart DK, Picca RA, Greaves J, Penner RM, Cioffi N (xullo de 2014). "Reduction of spectral interferences using ultraclean gold nanowire arrays in the LDI-MS analysis of a model peptide". Analytical and Bioanalytical Chemistry 406 (19): 4571–83. PMID 24980599. doi:10.1007/s00216-014-7876-7.

[pmid1064883-2] 2,0 ^2,1 Lazarus LH, Ling N, Guillemin R (xuño 1976). "beta-Lipotropin as a prohormone for the morphinomimetic peptides endorphins and enkephalins". Proceedings of the National Academy of Sciences of the United States of America 73 (6): 2156–9. Bibcode:1976PNAS...73.2156L. PMC 430469. PMID 1064883. doi:10.1073/pnas.73.6.2156.

[pmid9142421-3] Hughes J, Kosterlitz HW, Smith TW (febreiro de 1997). "The distribution of methionine-enkephalin and leucine-enkephalin in the brain and peripheral tissues. 1977". British Journal of Pharmacology 120 (4 Suppl): 428–36; discussion 426–7. PMC 3224324. PMID 9142421. doi:10.1111/j.1476-5381.1997.tb06829.x.

[pmid870028-4] Schiller PW, Yam CF, Lis M (maio de 1977). "Evidence for topographical analogy between methionine-enkephalin and morphine derivatives". Biochemistry 16 (9): 1831–8. PMID 870028. doi:10.1021/bi00628a011.

[pmid6086883-5] Porreca F, Mosberg HI, Hurst R, Hruby VJ, Burks TF (agosto de 1984). "Roles of mu, delta and kappa opioid receptors in spinal and supraspinal mediation of gastrointestinal transit effects and hot-plate analgesia in the mouse". The Journal of Pharmacology and Experimental Therapeutics 230 (2): 341–8. PMID 6086883.

[pmid8114680-6] Raynor K, Kong H, Chen Y, Yasuda K, Yu L, Bell GI, Reisine T (febreiro de 1994). "Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors". Molecular Pharmacology 45 (2): 330–4. PMID 8114680.

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Leu-encefalina

Nome IUPAC ácido (2R)-2-[[(2R)-2-[[2-[[2-[[(2R)-2-amino-3-(4-hidroxifenil)propanoil]amino]acetil]amino]acetil]amino]-3-fenilpropanoil]amino]-4-metilpentanoico
Outros nomes [Leu]encefalina; [Leu⁵]encefalina; leu-encefalina; leucina encefalina
Identificadores
Número CAS	58822-25-6
PubChem	461776
ChemSpider	406229
UNII	RI01R707R6
ChEBI	CHEBI:89656
ChEMBL	CHEMBL8234
Ligando IUPHAR	1613
Imaxes 3D Jmol	Image 1
SMILES O=C(O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)Cc2ccccc2)CC(C)C
InChI InChI=1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1 Key: URLZCHNOLZSCCA-VABKMULXSA-N InChI=1/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1 Key: URLZCHNOLZSCCA-VABKMULXBR
Propiedades
Fórmula molecular	C₂₈H₃₇N₅O₇
Masa molecular	555,62 g/mol^[1]
Se non se indica outra cousa, os datos están tomados en condicións estándar de 25 °C e 100 kPa.