Chemistry:Conantokin G

Conantokin G
Identifiers
	IUPAC name 2-[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-4-carboxybutanoyl]amino]-4,4-dicarboxybutanoyl]amino]-4,4-dicarboxybutanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoyl]amino]-4,4-dicarboxybutanoyl]amino]-4-oxobutanoyl]amino]-5-oxopentanoyl]amino]-4,4-dicarboxybutanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-[[(2S)-6-amino-1-[[(2S)-1-[[(1S)-3-amino-1-carboxy-3-oxopropyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-oxopropyl]propanedioic acid;
CAS Number	133628-78-1;
PubChem CID	16209752;
ChemSpider	17337884;
Chemical and physical data
Formula	C88H137N25O45
Molar mass	2265.194 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(C(=O)O)C(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C(=O)O)C(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(C(=O)O)C(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C(=O)O)C(=O)O)NC(=O)[C@H](CC(C(=O)O)C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)CN;
	InChI InChI=1S/C88H137N25O45/c1-7-34(6)61(76(136)102-41(12-10-20-97-88(95)96)62(122)105-47(23-35(77(137)138)78(139)140)68(128)99-40(11-8-9-19-89)63(123)112-54(31-114)75(135)111-53(87(157)158)29-58(94)118)113-74(134)46(22-33(4)5)104-69(129)48(24-36(79(141)142)80(143)144)107-66(126)44(14-17-56(92)116)101-73(133)52(28-57(93)117)110-72(132)50(26-38(83(149)150)84(151)152)108-65(125)43(13-16-55(91)115)100-67(127)45(21-32(2)3)103-70(130)51(27-39(85(153)154)86(155)156)109-71(131)49(25-37(81(145)146)82(147)148)106-64(124)42(15-18-60(120)121)98-59(119)30-90/h32-54,61,114H,7-31,89-90H2,1-6H3,(H2,91,115)(H2,92,116)(H2,93,117)(H2,94,118)(H,98,119)(H,99,128)(H,100,127)(H,101,133)(H,102,136)(H,103,130)(H,104,129)(H,105,122)(H,106,124)(H,107,126)(H,108,125)(H,109,131)(H,110,132)(H,111,135)(H,112,123)(H,113,134)(H,120,121)(H,137,138)(H,139,140)(H,141,142)(H,143,144)(H,145,146)(H,147,148)(H,149,150)(H,151,152)(H,153,154)(H,155,156)(H,157,158)(H4,95,96,97)/t34-,40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,61-/m0/s1; Key:MKBJAZBKZZICDG-QGXIKSNHSA-N;

Conantokin G is a naturally occurring 17-amino acid peptide isolated from the venom of the deadly marine cone snail Conus geographus. It has the amino acid sequence GEXXLQXNQXLIRXKSN, where X = gamma-Carboxyglutamic acid, a post-translationally modified derivative of glutamic acid with two COOH groups. It has sedative and analgesic effects in mice, acting as an NMDA receptor antagonist.^[1]^[2]^[3]^[4]^[5]^[6]

References

↑ "Conantokins: inhibitors of ion flow through the N-methyl-D-aspartate receptor channels". Current Drug Targets 1 (3): 219–235. November 2000. doi:10.2174/1389450003349218. PMID 11465072.
↑ "Structure-function relationships of the NMDA receptor antagonist conantokin peptides". Current Drug Targets 2 (3): 313–322. September 2001. doi:10.2174/1389450013348542. PMID 11554555.
↑ "Conantokins: peptide antagonists of NMDA receptors". Current Medicinal Chemistry 11 (23): 3073–3084. December 2004. doi:10.2174/0929867043363901. PMID 15579001.
↑ "Conantokin-G attenuates detrimental effects of NMDAR hyperactivity in an ischemic rat model of stroke". PLOS ONE 10 (3). 2015. doi:10.1371/journal.pone.0122840. PMID 25822337. Bibcode: 2015PLoSO..1022840B.
↑ "Antagonistic action on NMDA/GluN2B mediated currents of two peptides that were conantokin-G structure-based designed". BMC Neuroscience 18 (1). May 2017. doi:10.1186/s12868-017-0361-4. PMID 28511693.
↑ "Changes in NMDA Receptor Function in Rapid Ischemic Tolerance: A Potential Role for Tri-Heteromeric NMDA Receptors". Biomolecules 12 (9): 1214. September 2022. doi:10.3390/biom12091214. PMID 36139053.

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Original source: https://en.wikipedia.org/wiki/Conantokin G. Read more

[1] "Conantokins: inhibitors of ion flow through the N-methyl-D-aspartate receptor channels". Current Drug Targets 1 (3): 219–235. November 2000. doi:10.2174/1389450003349218. PMID 11465072.

[2] "Structure-function relationships of the NMDA receptor antagonist conantokin peptides". Current Drug Targets 2 (3): 313–322. September 2001. doi:10.2174/1389450013348542. PMID 11554555.

[3] "Conantokins: peptide antagonists of NMDA receptors". Current Medicinal Chemistry 11 (23): 3073–3084. December 2004. doi:10.2174/0929867043363901. PMID 15579001.

[4] "Conantokin-G attenuates detrimental effects of NMDAR hyperactivity in an ischemic rat model of stroke". PLOS ONE 10 (3). 2015. doi:10.1371/journal.pone.0122840. PMID 25822337. Bibcode: 2015PLoSO..1022840B.

[5] "Antagonistic action on NMDA/GluN2B mediated currents of two peptides that were conantokin-G structure-based designed". BMC Neuroscience 18 (1). May 2017. doi:10.1186/s12868-017-0361-4. PMID 28511693.

[6] "Changes in NMDA Receptor Function in Rapid Ischemic Tolerance: A Potential Role for Tri-Heteromeric NMDA Receptors". Biomolecules 12 (9): 1214. September 2022. doi:10.3390/biom12091214. PMID 36139053.

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Identifiers

IUPAC name 2-[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-4-carboxybutanoyl]amino]-4,4-dicarboxybutanoyl]amino]-4,4-dicarboxybutanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoyl]amino]-4,4-dicarboxybutanoyl]amino]-4-oxobutanoyl]amino]-5-oxopentanoyl]amino]-4,4-dicarboxybutanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-[[(2S)-6-amino-1-[[(2S)-1-[[(1S)-3-amino-1-carboxy-3-oxopropyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-oxopropyl]propanedioic acid
CAS Number	133628-78-1
PubChem CID	16209752
ChemSpider	17337884
Chemical and physical data
Formula	C₈₈H₁₃₇N₂₅O₄₅
Molar mass	2265.194 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(C(=O)O)C(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C(=O)O)C(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(C(=O)O)C(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C(=O)O)C(=O)O)NC(=O)[C@H](CC(C(=O)O)C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)CN
InChI InChI=1S/C88H137N25O45/c1-7-34(6)61(76(136)102-41(12-10-20-97-88(95)96)62(122)105-47(23-35(77(137)138)78(139)140)68(128)99-40(11-8-9-19-89)63(123)112-54(31-114)75(135)111-53(87(157)158)29-58(94)118)113-74(134)46(22-33(4)5)104-69(129)48(24-36(79(141)142)80(143)144)107-66(126)44(14-17-56(92)116)101-73(133)52(28-57(93)117)110-72(132)50(26-38(83(149)150)84(151)152)108-65(125)43(13-16-55(91)115)100-67(127)45(21-32(2)3)103-70(130)51(27-39(85(153)154)86(155)156)109-71(131)49(25-37(81(145)146)82(147)148)106-64(124)42(15-18-60(120)121)98-59(119)30-90/h32-54,61,114H,7-31,89-90H2,1-6H3,(H2,91,115)(H2,92,116)(H2,93,117)(H2,94,118)(H,98,119)(H,99,128)(H,100,127)(H,101,133)(H,102,136)(H,103,130)(H,104,129)(H,105,122)(H,106,124)(H,107,126)(H,108,125)(H,109,131)(H,110,132)(H,111,135)(H,112,123)(H,113,134)(H,120,121)(H,137,138)(H,139,140)(H,141,142)(H,143,144)(H,145,146)(H,147,148)(H,149,150)(H,151,152)(H,153,154)(H,155,156)(H,157,158)(H4,95,96,97)/t34-,40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,61-/m0/s1 Key:MKBJAZBKZZICDG-QGXIKSNHSA-N

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