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Volumn 45, Issue 4, 2013, Pages 821-833

A new method to synthesize creatine derivatives

Author keywords

Creatine; Creatine derivatives synthesis; Creatine reactivity; Guanidine group

Indexed keywords

AMIDE; AMINO ACID DERIVATIVE; BUTOXYCARBONYL DERIVATIVE; CARBONYL DERIVATIVE; CARBOXYLIC DERIVATIVE; CREATINE DERIVATIVE; CREATININE; GUANIDINE DERIVATIVE; ORGANIC SOLVENT; UNCLASSIFIED DRUG;

EID: 84885309241     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-013-1525-x     Document Type: Article
Times cited : (5)

References (38)
  • 1
    • 65249129156 scopus 로고    scopus 로고
    • Creatine and its potential therapeutic value for targeting cellular energy impairment in neurodegenerative diseases
    • 10.1007/s12017-008-8053-y 19005780 10.1007/s12017-008-8053-y 1:CAS:528:DC%2BD1MXhtlKktA%3D%3D
    • Adhihetty P, Beal M (2008) Creatine and its potential therapeutic value for targeting cellular energy impairment in neurodegenerative diseases. Neuromolecular Med 10(4):275-290. doi: 10.1007/s12017-008-8053-y
    • (2008) Neuromolecular Med , vol.10 , Issue.4 , pp. 275-290
    • Adhihetty, P.1    Beal, M.2
  • 2
    • 83055186656 scopus 로고    scopus 로고
    • Searching for a therapy of creatine transporter deficiency: Some effects of creatine ethyl ester in brain slices in vitro
    • 10.1016/j.neuroscience.2011.09.018 21963865 10.1016/j.neuroscience.2011. 09.018 1:CAS:528:DC%2BC3MXhs1SgsL3M
    • Adriano E, Garbati P, Damonte G, Salis A, Armirotti A, Balestrino M (2011) Searching for a therapy of creatine transporter deficiency: some effects of creatine ethyl ester in brain slices in vitro. Neuroscience 199:386-393. doi: 10.1016/j.neuroscience.2011.09.018
    • (2011) Neuroscience , vol.199 , pp. 386-393
    • Adriano, E.1    Garbati, P.2    Damonte, G.3    Salis, A.4    Armirotti, A.5    Balestrino, M.6
  • 3
    • 43849087699 scopus 로고    scopus 로고
    • Functions and effects of creatine in the central nervous system
    • 10.1016/j.brainresbull.2008.02.035 18502307 10.1016/j.brainresbull.2008. 02.035 1:CAS:528:DC%2BD1cXmtlWht70%3D
    • Andres RH, Ducray AD, Schlattner U, Wallimann T, Widmer HR (2008) Functions and effects of creatine in the central nervous system. Brain Res Bull 76:329-343. doi: 10.1016/j.brainresbull.2008.02.035
    • (2008) Brain Res Bull , vol.76 , pp. 329-343
    • Andres, R.H.1    Ducray, A.D.2    Schlattner, U.3    Wallimann, T.4    Widmer, H.R.5
  • 4
    • 0036391841 scopus 로고    scopus 로고
    • Role of creatine and phosphocreatine in neuronal protection from anoxic and ischemic damage
    • 10.1007/s00726-001-0133-3 12373542 10.1007/s00726-001-0133-3 1:CAS:528:DC%2BD38Xns1Gnsbs%3D
    • Balestrino M, Lensman M, Parodi M, Perasso L, Rebaudo R, Melani R, Polenov S, Cupello A (2002) Role of creatine and phosphocreatine in neuronal protection from anoxic and ischemic damage. Amino Acids 23(1-3):221-229. doi: 10.1007/s00726-001-0133-3
    • (2002) Amino Acids , vol.23 , Issue.1-3 , pp. 221-229
    • Balestrino, M.1    Lensman, M.2    Parodi, M.3    Perasso, L.4    Rebaudo, R.5    Melani, R.6    Polenov, S.7    Cupello, A.8
  • 5
    • 80052809265 scopus 로고    scopus 로고
    • Neuroprotective effects of creatine
    • doi: 10.1007/s00726-011-0851-0
    • Beal M (2011) Neuroprotective effects of creatine. Amino Acids 1-9. doi: 10.1007/s00726-011-0851-0
    • (2011) Amino Acids , pp. 1-9
    • Beal, M.1
  • 6
    • 79961172469 scopus 로고    scopus 로고
    • Creatinyl amino acids - New hybrid compounds with neuroprotective activity
    • 10.1002/psc.1379 21644247 10.1002/psc.1379 1:CAS:528:DC%2BC3MXntVWjsLY%3D
    • Burov S, Leko M, Dorosh M, Dobrodumov A, Veselkina O (2011a) Creatinyl amino acids - new hybrid compounds with neuroprotective activity. J Pept Sci 17(9):620-626. doi: 10.1002/psc.1379
    • (2011) J Pept Sci , vol.17 , Issue.9 , pp. 620-626
    • Burov, S.1    Leko, M.2    Dorosh, M.3    Dobrodumov, A.4    Veselkina, O.5
  • 8
    • 0027441062 scopus 로고
    • The 2,2,4,6,7, pentamethyldihydrobenzofuran-5-sulfonyl group (Pbf) as arginine side chain protectant
    • 10.1016/S0040-4039(00)61487-9 10.1016/S0040-4039(00)61487-9 1:CAS:528:DyaK2cXislWisbg%3D
    • Carpino LA, Shroff H, Triolo SA, Mansour ESME, Wenschuh H, Albericio F (1993) The 2,2,4,6,7, pentamethyldihydrobenzofuran-5-sulfonyl group (Pbf) as arginine side chain protectant. Tetrahedron Lett 34(49):7829-7832. doi: 10.1016/S0040-4039(00)61487-9
    • (1993) Tetrahedron Lett , vol.34 , Issue.49 , pp. 7829-7832
    • Carpino, L.A.1    Shroff, H.2    Triolo, S.A.3    Mansour, E.4    Wenschuh, H.5    Albericio, F.6
  • 9
    • 0037525384 scopus 로고    scopus 로고
    • Using mixed anhydrides from amino acids and isobutyl chloroformate in N-acylations: A case study on the elucidation of mechanism of urethane formation and starting amino acid liberation using carbon dioxide as the probe
    • 10.1016/S0040-4039(03)01329-7 10.1016/S0040-4039(03)01329-7 1:CAS:528:DC%2BD3sXkvVGrsLY%3D
    • Chaudhary A, Girgis M, Prashad M, Hu B, Har D, Repič O, Blacklock TJ (2003) Using mixed anhydrides from amino acids and isobutyl chloroformate in N-acylations: a case study on the elucidation of mechanism of urethane formation and starting amino acid liberation using carbon dioxide as the probe. Tetrahedron Lett 44(29):5543-5546. doi: 10.1016/S0040-4039(03)01329-7
    • (2003) Tetrahedron Lett , vol.44 , Issue.29 , pp. 5543-5546
    • Chaudhary, A.1    Girgis, M.2    Prashad, M.3    Hu, B.4    Har, D.5    Repič, O.6    Blacklock, T.J.7
  • 10
    • 0035854314 scopus 로고    scopus 로고
    • Solution synthesis and characterization of aza-beta(3)-peptides (N(alpha)-substituted hydrazino acetic acid oligomers)
    • 11442427 10.1021/jo001500d 1:CAS:528:DC%2BD3MXksVSjur4%3D
    • Cheguillaume A, Salaün A, Sinbandhit S, Potel M, Gall P, Baudy-Floćh M, Le Grel P (2001) Solution synthesis and characterization of aza-beta(3)-peptides (N(alpha)-substituted hydrazino acetic acid oligomers). J Org Chem 66(14):4923-4929
    • (2001) J Org Chem , vol.66 , Issue.14 , pp. 4923-4929
    • Cheguillaume, A.1    Salaün, A.2    Sinbandhit, S.3    Potel, M.4    Gall, P.5    Baudy-Floćh, M.6    Le Grel, P.7
  • 11
    • 0032784879 scopus 로고    scopus 로고
    • A facile method for the transformation of N-(tert-butoxycarbonyl)α- amino acids to N-unprotected α-amino acids methyl esters
    • 10.1021/jo990311w 10.1021/jo990311w 1:CAS:528:DyaK1MXnsFCqsb4%3D
    • Chen BC, Skoumbourdis AP, Guo P, Bednarz MS, Kocy OR, Sundeen JE, Vite GD (1999) A facile method for the transformation of N-(tert-butoxycarbonyl) α-amino acids to N-unprotected α-amino acids methyl esters. J Org Chem 64:9294-9296. doi: 10.1021/jo990311w
    • (1999) J Org Chem , vol.64 , pp. 9294-9296
    • Chen, B.C.1    Skoumbourdis, A.P.2    Guo, P.3    Bednarz, M.S.4    Kocy, O.R.5    Sundeen, J.E.6    Vite, G.D.7
  • 12
    • 0037205815 scopus 로고    scopus 로고
    • A simple LC method with UV detection for the analysis of creatine and creatinine and its application to several creatine formulations
    • 10.1016/S0731-7085(02)00167-X 12093528 10.1016/S0731-7085(02)00167-X 1:CAS:528:DC%2BD38XkvFyrur8%3D
    • Dash AK, Sawhney A (2002) A simple LC method with UV detection for the analysis of creatine and creatinine and its application to several creatine formulations. J Pharm Biomed Anal 29(5):939-945. doi: 10.1016/S0731-7085(02) 00167-X
    • (2002) J Pharm Biomed Anal , vol.29 , Issue.5 , pp. 939-945
    • Dash, A.K.1    Sawhney, A.2
  • 13
    • 33947490630 scopus 로고
    • The equilibrium between creatine and creatinine in aqueous solution. The effect of the hydrogen ion
    • 10.1021/ja01681a040 1:CAS:528:DyaB2MXhtFOqsw%3D%3D
    • Edgar G, Shiver HE (1925) The equilibrium between creatine and creatinine in aqueous solution. The effect of the hydrogen ion. J Am Chem Soc 47(4):1179-1188
    • (1925) J Am Chem Soc , vol.47 , Issue.4 , pp. 1179-1188
    • Edgar, G.1    Shiver, H.E.2
  • 14
    • 0035893870 scopus 로고    scopus 로고
    • The creatine-phosphocreatine system: There's more than one song in its repertoire
    • 10.1113/jphysiol.2001.013478 10.1113/jphysiol.2001.013478 1:CAS:528:DC%2BD38XntVGmsA%3D%3D
    • Greenhaff PL (2001) The creatine-phosphocreatine system: there's more than one song in its repertoire. J Physiol (Lond) 537(3):657. doi: 10.1113/jphysiol.2001.013478
    • (2001) J Physiol (Lond) , vol.537 , Issue.3 , pp. 657
    • Greenhaff, P.L.1
  • 16
    • 67649274217 scopus 로고    scopus 로고
    • Amino acid-protecting groups
    • 10.1021/cr800323s 19364121 10.1021/cr800323s 1:CAS:528: DC%2BD1MXksVSlur4%3D
    • Isidro-Llobet A, Alvarez M, Albericio F (2009) Amino acid-protecting groups. Chem Rev 109:2455-2504. doi: 10.1021/cr800323s
    • (2009) Chem Rev , vol.109 , pp. 2455-2504
    • Isidro-Llobet, A.1    Alvarez, M.2    Albericio, F.3
  • 17
    • 44449160328 scopus 로고    scopus 로고
    • A convenient synthesis of amino acid methyl esters
    • 10.3390/molecules13051111 18560331 10.3390/molecules13051111 1:CAS:528:DC%2BD1cXmvVSlsrY%3D
    • Li J, Sha Y (2008) A convenient synthesis of amino acid methyl esters. Molecules 13(5):1111-1119. doi: 10.3390/molecules13051111
    • (2008) Molecules , vol.13 , Issue.5 , pp. 1111-1119
    • Li, J.1    Sha, Y.2
  • 18
    • 33750297109 scopus 로고    scopus 로고
    • The creatine transporter mediates the uptake of creatine by brain tissue, but not the uptake of two creatine-derived compounds
    • 10.1016/j.neuroscience.2006.06.058 16949212 10.1016/j.neuroscience.2006. 06.058 1:CAS:528:DC%2BD28XhtFCjsbzP
    • Lunardi G, Parodi A, Perasso L, Pohvozcheva AV, Scarrone S, Adriano E, Florio T, Gandolfo C, Cupello A, Burov SV, Balestrino M (2006) The creatine transporter mediates the uptake of creatine by brain tissue, but not the uptake of two creatine-derived compounds. Neuroscience 142(4):991-997. doi: 10.1016/j.neuroscience.2006.06.058
    • (2006) Neuroscience , vol.142 , Issue.4 , pp. 991-997
    • Lunardi, G.1    Parodi, A.2    Perasso, L.3    Pohvozcheva, A.V.4    Scarrone, S.5    Adriano, E.6    Florio, T.7    Gandolfo, C.8    Cupello, A.9    Burov, S.V.10    Balestrino, M.11
  • 19
    • 76249097469 scopus 로고    scopus 로고
    • Creatine and Creatine Deficiency Syndromes: Biochemical and clinical aspects
    • 10.1016/j.pediatrneurol.2009.07.015 20159424 10.1016/j.pediatrneurol. 2009.07.015
    • Nasrallah F, Feki M, Kaabachi N (2010) Creatine and Creatine Deficiency Syndromes: biochemical and clinical aspects. Pediatr Neurol 42(3):163-171. doi: 10.1016/j.pediatrneurol.2009.07.015
    • (2010) Pediatr Neurol , vol.42 , Issue.3 , pp. 163-171
    • Nasrallah, F.1    Feki, M.2    Kaabachi, N.3
  • 21
    • 0031906453 scopus 로고    scopus 로고
    • Acetyl chloride-methanol as a convenient reagent for: A) quantitative formation of amine hydrochlorides; B) carboxylate ester formation; C) mild removal of N-t-Boc-protective group
    • 10.1080/00397919808005101 10.1080/00397919808005101 1:CAS:528: DyaK1cXhsVCrs7o%3D
    • Nudelman A, Bechor Y, Falb E, Fischer B, Wexler BA, Nudelman A (1998) Acetyl chloride-methanol as a convenient reagent for: A) quantitative formation of amine hydrochlorides; B) carboxylate ester formation; C) mild removal of N-t-Boc-protective group. Synth Commun 28(3):471-474. doi: 10.1080/ 00397919808005101
    • (1998) Synth Commun , vol.28 , Issue.3 , pp. 471-474
    • Nudelman, A.1    Bechor, Y.2    Falb, E.3    Fischer, B.4    Wexler, B.A.5    Nudelman, A.6
  • 22
    • 0036843535 scopus 로고    scopus 로고
    • The blood-brain barrier creatine transporter is a major pathway for supplying creatine to the brain
    • 12439290 10.1097/00004647-200211000-00006 1:CAS:528:DC%2BD38Xosl2gtrc%3D
    • Ohtsuki S, Tachikawa M, Takanaga T, Shimizu H, Watanabe TM, Hosoya K, Terasaki T (2002) The blood-brain barrier creatine transporter is a major pathway for supplying creatine to the brain. J Cereb Blood Flow Metab 22(11):1327-1335
    • (2002) J Cereb Blood Flow Metab , vol.22 , Issue.11 , pp. 1327-1335
    • Ohtsuki, S.1    Tachikawa, M.2    Takanaga, T.3    Shimizu, H.4    Watanabe, T.M.5    Hosoya, K.6    Terasaki, T.7
  • 23
    • 0038665436 scopus 로고    scopus 로고
    • Kinetics of creatine in blood and brain after intraperitoneal injection in the rat
    • 10.1016/S0006-8993(03)02547-2 12742622 10.1016/S0006-8993(03)02547-2 1:CAS:528:DC%2BD3sXjs1Cktrg%3D
    • Perasso L, Cupello A, Lunardi GL, Principato C, Gandolfo C, Balestrino M (2003) Kinetics of creatine in blood and brain after intraperitoneal injection in the rat. Brain Res 974(1-2):37-42. doi: 10.1016/S0006-8993(03)02547-2
    • (2003) Brain Res , vol.974 , Issue.1-2 , pp. 37-42
    • Perasso, L.1    Cupello, A.2    Lunardi, G.L.3    Principato, C.4    Gandolfo, C.5    Balestrino, M.6
  • 25
    • 84873987487 scopus 로고    scopus 로고
    • Therapeutic use of creatine in brain or heart ischemia: Available data and future perspectives
    • 10.1002/med.20255 22135003 10.1002/med.20255 1:CAS:528: DC%2BC3sXivFartLc%3D
    • Perasso L, Spallarossa P, Gandolfo C, Ruggeri P, Balestrino M (2013) Therapeutic use of creatine in brain or heart ischemia: available data and future perspectives. Med Res Rev 33(2):336-363. doi: 10.1002/med.20255
    • (2013) Med Res Rev , vol.33 , Issue.2 , pp. 336-363
    • Perasso, L.1    Spallarossa, P.2    Gandolfo, C.3    Ruggeri, P.4    Balestrino, M.5
  • 29
    • 0037459670 scopus 로고    scopus 로고
    • Phase-transfer-catalyzed alkylation of guanidines by alkyl halides under biphasic conditions: A convenient protocol for the synthesis of highly functionalized guanidines
    • 10.1021/jo0265535 12636395 10.1021/jo0265535 1:CAS:528: DC%2BD3sXht1Sgtbc%3D
    • Powell DA, Ramsden PD, Batey RA (2003) Phase-transfer-catalyzed alkylation of guanidines by alkyl halides under biphasic conditions: a convenient protocol for the synthesis of highly functionalized guanidines. J Org Chem 68(6):2300-2309. doi: 10.1021/jo0265535
    • (2003) J Org Chem , vol.68 , Issue.6 , pp. 2300-2309
    • Powell, D.A.1    Ramsden, P.D.2    Batey, R.A.3
  • 30
    • 0030948518 scopus 로고    scopus 로고
    • Solid phase of guanidines
    • 10.1016/S0040-4020(97)00225-1 10.1016/S0040-4020(97)00225-1 1:CAS:528:DyaK2sXjtlKhu74%3D
    • Robinson S, Roskamp EJ (1997) Solid phase of guanidines. Tetrahedron 53(19):6697-6705. doi: 10.1016/S0040-4020(97)00225-1
    • (1997) Tetrahedron , vol.53 , Issue.19 , pp. 6697-6705
    • Robinson, S.1    Roskamp, E.J.2
  • 32
    • 0037306564 scopus 로고    scopus 로고
    • Creatine deficiency syndromes
    • 10.1023/A:1022443503883 12701824 10.1023/A:1022443503883 1:CAS:528:DC%2BD3sXht12jtrk%3D
    • Schulze A (2003) Creatine deficiency syndromes. Mol Cell Biochem 244(1-2):143-150. doi: 10.1023/A:1022443503883
    • (2003) Mol Cell Biochem , vol.244 , Issue.1-2 , pp. 143-150
    • Schulze, A.1
  • 34
    • 0037027845 scopus 로고    scopus 로고
    • Separation methods applicable to urinary creatine and creatinine
    • 10.1016/S1570-0232(02)00617-7 12450655 1:CAS:528:DC%2BD3sXktFCjtA%3D%3D
    • Smith-Palmer T (2002) Separation methods applicable to urinary creatine and creatinine. J Chromatogr B Analyt Technol Biomed Life Sci 781(1-2):93-106. doi: 10.1016/S1570-0232(02)00617-7
    • (2002) J Chromatogr B Analyt Technol Biomed Life Sci , vol.781 , Issue.1-2 , pp. 93-106
    • Smith-Palmer, T.1
  • 35
    • 0034787869 scopus 로고    scopus 로고
    • Creatine and the creatine transporter: A review
    • 10.1023/A:1011908606819 11693194 10.1023/A:1011908606819 1:CAS:528:DC%2BD3MXot1Ciu78%3D
    • Snow RJ, Murphy RM (2001) Creatine and the creatine transporter: a review. Mol Cell Biochem 224(1-2):169-181. doi: 10.1023/A:1011908606819
    • (2001) Mol Cell Biochem , vol.224 , Issue.1-2 , pp. 169-181
    • Snow, R.J.1    Murphy, R.M.2
  • 36
    • 79952186878 scopus 로고    scopus 로고
    • Synthesis and biological activity of amino acid conjugates of abscisic acid
    • 10.1016/j.bmc.2011.01.019 21310619 10.1016/j.bmc.2011.01.019 1:CAS:528:DC%2BC3MXisFyltLw%3D
    • Todoroki Y, Narita K, Muramatsu T, Shimomura H, Ohnishi T, Mizutani M, Ueno K, Hirai N (2011) Synthesis and biological activity of amino acid conjugates of abscisic acid. Bioorg Med Chem 19:1743-1750. doi: 10.1016/j.bmc.2011.01.019
    • (2011) Bioorg Med Chem , vol.19 , pp. 1743-1750
    • Todoroki, Y.1    Narita, K.2    Muramatsu, T.3    Shimomura, H.4    Ohnishi, T.5    Mizutani, M.6    Ueno, K.7    Hirai, N.8
  • 38
    • 0034597978 scopus 로고    scopus 로고
    • Aqueous trifluoroacetic acid - An efficient reagent for exclusively cleaving the 5′-end of 3′,5′-TIPDS protected ribonucleosides
    • 10.1016/S0040-4039(00)01685-3 1:CAS:528:DC%2BD3cXovFOmsL4%3D
    • Zhu XF, Williams HJ, Scott AI (2000) Aqueous trifluoroacetic acid - an efficient reagent for exclusively cleaving the 5′-end of 3′,5′-TIPDS protected ribonucleosides. Tetrahedron Lett 41(49):9541-9545
    • (2000) Tetrahedron Lett , vol.41 , Issue.49 , pp. 9541-9545
    • Zhu, X.F.1    Williams, H.J.2    Scott, A.I.3


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