Leumorphin

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Leumorphin
Names
IUPAC name
L-Tyrosylglycylglycyl-L-phenylalanyl-L-leucyl-L-arginyl-L-arginyl-L-glutaminyl-L-phenylalanyl-L-lysyl-L-valyl-L-valyl-L-threonyl-L-arginyl-L-seryl-L-glutaminyl-L-α-glutamyl-L-α-aspartyl-L-prolyl-L-asparaginyl-L-alanyl-L-tyrosyl-L-serylglycyl-L-α-glutamyl-L-leucyl-L-phenylalanyl-L-α-aspartyl-L-alanine
Other names
Dynorphin B-29; Dynorphin B (1–29)
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C150H224N42O46/c1-74(2)59-97(181-137(227)99(62-81-27-15-12-16-28-81)171-113(202)70-165-112(201)69-166-123(213)88(152)61-84-38-42-86(196)43-39-84)135(225)174-91(35-24-56-163-149(158)159)125(215)172-90(34-23-55-162-148(156)157)126(216)175-95(47-51-110(154)199)130(220)182-101(63-82-29-17-13-18-30-82)138(228)173-89(33-21-22-54-151)132(222)189-119(76(5)6)143(233)190-120(77(7)8)144(234)191-121(80(11)195)145(235)178-92(36-25-57-164-150(160)161)127(217)188-107(73-194)141(231)177-94(46-50-109(153)198)129(219)176-96(49-53-116(206)207)131(221)186-105(68-118(210)211)146(236)192-58-26-37-108(192)142(232)185-103(66-111(155)200)133(223)168-78(9)122(212)179-100(65-85-40-44-87(197)45-41-85)140(230)187-106(72-193)124(214)167-71-114(203)170-93(48-52-115(204)205)128(218)180-98(60-75(3)4)136(226)183-102(64-83-31-19-14-20-32-83)139(229)184-104(67-117(208)209)134(224)169-79(10)147(237)238/h12-20,27-32,38-45,74-80,88-108,119-121,193-197H,21-26,33-37,46-73,151-152H2,1-11H3,(H2,153,198)(H2,154,199)(H2,155,200)(H,165,201)(H,166,213)(H,167,214)(H,168,223)(H,169,224)(H,170,203)(H,171,202)(H,172,215)(H,173,228)(H,174,225)(H,175,216)(H,176,219)(H,177,231)(H,178,235)(H,179,212)(H,180,218)(H,181,227)(H,182,220)(H,183,226)(H,184,229)(H,185,232)(H,186,221)(H,187,230)(H,188,217)(H,189,222)(H,190,233)(H,191,234)(H,204,205)(H,206,207)(H,208,209)(H,210,211)(H,237,238)(H4,156,157,162)(H4,158,159,163)(H4,160,161,164)/t78-,79-,80+,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,119-,120-,121-/m0/s1
    Key: NVEXXUGCBSXDLS-LNEXRSTESA-N
  • InChI=1/C150H224N42O46/c1-74(2)59-97(181-137(227)99(62-81-27-15-12-16-28-81)171-113(202)70-165-112(201)69-166-123(213)88(152)61-84-38-42-86(196)43-39-84)135(225)174-91(35-24-56-163-149(158)159)125(215)172-90(34-23-55-162-148(156)157)126(216)175-95(47-51-110(154)199)130(220)182-101(63-82-29-17-13-18-30-82)138(228)173-89(33-21-22-54-151)132(222)189-119(76(5)6)143(233)190-120(77(7)8)144(234)191-121(80(11)195)145(235)178-92(36-25-57-164-150(160)161)127(217)188-107(73-194)141(231)177-94(46-50-109(153)198)129(219)176-96(49-53-116(206)207)131(221)186-105(68-118(210)211)146(236)192-58-26-37-108(192)142(232)185-103(66-111(155)200)133(223)168-78(9)122(212)179-100(65-85-40-44-87(197)45-41-85)140(230)187-106(72-193)124(214)167-71-114(203)170-93(48-52-115(204)205)128(218)180-98(60-75(3)4)136(226)183-102(64-83-31-19-14-20-32-83)139(229)184-104(67-117(208)209)134(224)169-79(10)147(237)238/h12-20,27-32,38-45,74-80,88-108,119-121,193-197H,21-26,33-37,46-73,151-152H2,1-11H3,(H2,153,198)(H2,154,199)(H2,155,200)(H,165,201)(H,166,213)(H,167,214)(H,168,223)(H,169,224)(H,170,203)(H,171,202)(H,172,215)(H,173,228)(H,174,225)(H,175,216)(H,176,219)(H,177,231)(H,178,235)(H,179,212)(H,180,218)(H,181,227)(H,182,220)(H,183,226)(H,184,229)(H,185,232)(H,186,221)(H,187,230)(H,188,217)(H,189,222)(H,190,233)(H,191,234)(H,204,205)(H,206,207)(H,208,209)(H,210,211)(H,237,238)(H4,156,157,162)(H4,158,159,163)(H4,160,161,164)/t78-,79-,80+,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,119-,120-,121-/m0/s1
    Key: NVEXXUGCBSXDLS-LNEXRSTEBX
  • C[C@H]([C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(=O)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc2ccc(cc2)O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C)C(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc4ccccc4)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc5ccccc5)NC(=O)CNC(=O)CNC(=O)[C@H](Cc6ccc(cc6)O)N)O
Properties
C161H236N42O48
Molar mass 3527.85 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Leumorphin, also known as dynorphin B1–29, is a naturally occurring endogenous opioid peptide.[1][2][3] Derived as a proteolytic cleavage product of residues 226-254 of prodynorphin (preproenkephalin B),[4][5] leumorphin is a nonacosapeptide (29 amino acids in length) and has the sequence Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Gln-Phe-Lys-Val-Val-Thr-Arg-Ser-Gln-Glu-Asp-Pro-Asn-Ala-Tyr-Ser-Gly-Glu-Leu-Phe-Asp-Ala. It can be further reduced to dynorphin B (dynorphin B-13) and dynorphin B-14 by pitrilysin metallopeptidase 1 (formerly referred to as "dynorphin-converting enzyme"), an enzyme of the endopeptidase family.[6][7][8] Leumorphin behaves as a potent and selective κ-opioid receptor agonist, similarly to other endogenous opioid peptide derivatives of prodynorphin.[9][10]

See also

References

  1. ^ Schwarzer C (September 2009). "30 years of dynorphins—new insights on their functions in neuropsychiatric diseases". Pharmacology & Therapeutics. 123 (3): 353–370. doi:10.1016/j.pharmthera.2009.05.006. PMC 2872771. PMID 19481570.
  2. ^ Nakao K, Suda M, Sakamoto M, et al. (December 1983). "Leumorphin is a novel endogenous opioid peptide derived from preproenkephalin B". Biochemical and Biophysical Research Communications. 117 (3): 695–701. doi:10.1016/0006-291X(83)91653-4. PMID 6689399.
  3. ^ Suda M, Nakao K, Sakamoto M, et al. (August 1984). "Leumorphin is a novel endogenous opioid peptide in man". Biochemical and Biophysical Research Communications. 123 (1): 148–155. doi:10.1016/0006-291X(84)90392-9. PMID 6548137.
  4. ^ Leon F. Tseng (1 September 1995). Pharmacology of Opioid Peptides. CRC Press. p. 171. ISBN 978-3-7186-5632-5. Retrieved 22 April 2012.
  5. ^ Nock B, Giordano AL, Cicero TJ, O'Connor LH (August 1990). "Affinity of drugs and peptides for U-69,593-sensitive and -insensitive kappa opiate binding sites: the U-69,593-insensitive site appears to be the beta endorphin-specific epsilon receptor". The Journal of Pharmacology and Experimental Therapeutics. 254 (2): 412–9. PMID 2166790.
  6. ^ Devi L, Gupta P, Fricker LD (January 1991). "Subcellular localization, partial purification, and characterization of a dynorphin processing endopeptidase from bovine pituitary". Journal of Neurochemistry. 56 (1): 320–9. doi:10.1111/j.1471-4159.1991.tb02598.x. PMID 1670956. S2CID 19564095.
  7. ^ Berman YL, Juliano L, Devi LA (October 1995). "Purification and characterization of a dynorphin-processing endopeptidase". The Journal of Biological Chemistry. 270 (40): 23845–50. doi:10.1074/jbc.270.40.23845. PMID 7559562.
  8. ^ Mzhavia N, Berman YL, Qian Y, Yan L, Devi LA (May 1999). "Cloning, expression, and characterization of human metalloprotease 1: a novel member of the pitrilysin family of metalloendoproteases". DNA and Cell Biology. 18 (5): 369–80. doi:10.1089/104454999315268. PMID 10360838.
  9. ^ Suda M, Nakao K, Yoshimasa T, et al. (September 1984). "Human leumorphin is a potent, kappa opioid receptor agonist". Neuroscience Letters. 50 (1–3): 49–52. doi:10.1016/0304-3940(84)90460-9. PMID 6149506. S2CID 42419724.
  10. ^ Inenaga K, Nagatomo T, Nakao K, Yanaihara N, Yamashita H (January 1994). "Kappa-selective agonists decrease postsynaptic potentials and calcium components of action potentials in the supraoptic nucleus of rat hypothalamus in vitro". Neuroscience. 58 (2): 331–40. doi:10.1016/0306-4522(94)90039-6. PMID 7908725. S2CID 24631286.
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