VZL 2010, 79(4):151-156

Beta-Amino Acids and Their Natural Biologically Active Derivatives. IV. Derivatives of Unusual Acyclic Beta-Amino Acids

Jiří Patočka ORCID...
Jihočeská univerzita v Českých Budějovicích, Zdravotně sociální fakulta, katedra radiologie a toxikologie, České Budějovice
Vysoká škola aplikovaných ekonomických studií, s. r. o., Praha

Beta-aminokyseliny jsou v současné době předmětem rostoucího zájmu, a to nejen pro jejich přírodní úlohu, ale také pro jejich využití při syntéze peptidů. Kromě β-analogů přírodních α-aminokyselin jsou známy rozmanité neobvyklé alifatické β-aminokyseliny. Liší se délkou řetězce a v některých případech mají další methylové skupiny, nejrůznější funkční skupiny nebo dvojné či trojné vazby. Ačkoli neobvyklé acyklické β-aminokyseliny nejsou tak hojné jako jejich α-analogy, jsou také přítomny ve složitějších strukturách, jako jsou peptidy a depsipeptidy a mnohé z nich mají zajímavé farmakologické účinky, často související právě s jejich β-aminokyselinovou substrukturou.

Keywords: Neobvyklé β-aminokyseliny; Přírodní aminokyseliny; Peptidy; Depsipeptidy; Antibiotika; Ituriny; Kryptofycin; Amastatin; Ulongamidy

Beta-amino acids are currently of growing interest, not only because of their natural roles, but also for its use in peptide synthesis. Except of natural α-amino acid β-analogues, a variety of unusual aliphatic β-amino acids are known. They differ in respect to their chain length and possess, in some cases, additional methyl groups, different functional groups or a double or triple bond. Unusual acyclic β-amino acids, although less abundant than their α-analogues, are also present in more complex structures like peptides and depsipeptides, and many of them show interesting pharmacological effects that are often crucially based on their β-amino acid sub-structures.

Keywords: Unusual β-amino acids; Natural amino acids; Peptides; Depsipeptides; Antibiotics; Iturins; Cryptophycine; Amastatin; Ulongamides

Received: October 14, 2009; Published: December 1, 2010  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Patočka, J. (2010). Beta-Amino Acids and Their Natural Biologically Active Derivatives. IV. Derivatives of Unusual Acyclic Beta-Amino Acids. Vojenské Zdravotnické Listy, 79(4), 151-156
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    References

    1. AGAMI, C. - CHERAMI, S. - DECHOUX, L., et al. Enantioselective synthesis of α,β-substituted β-amino acids. Tetrahedron, 2001, vol. 57, p. 195-200. Go to original source...
    2. ANDERS, R. - KLEIMAN, J. - NICHOLSON, N., et al. Xemilofiban/orbofiban: insight into drug development. Cardiovasc. Drug Rev., 2001, vol. 19, no 2, p. 116-132. Go to original source... Go to PubMed...
    3. AUCLAIR, MC. - ADOLPHE, M. - GUILLOU, Y., et al. Effect of phascoline and phascolosomine, new natural guanide derivatives, on cultured rat cardiac cells. [Article in Franch] C. R. Seances Soc. Biol. Fil., 1976, vol. 170, no. 1, p. 65-70. Go to PubMed...
    4. BARCELOUX, DG. Grass pea and neurolathyrism (Lathyrus sativus L.). Dis. Mon., 2009, vol. 55, no. 6, p. 365-372. Go to original source... Go to PubMed...
    5. BARRET, GC. (Ed.) Amino Acid Derivatives. Practical Approach in Chemistry. 2nd Ed., New York, Oxford Univ Press, 2001. 270 p.
    6. BEDDOW, JE. - DAVIES, SG. - SMITH, AD., et al. Asymmetric synthesis of 2-alkyl- and 2-aryl-3-aminopropionic acids (beta2-amino acids) from (S)-N-acryloyl-5,5-dimethyloxazolidin-2-one SuperQuat derivatives. Chem. Commun. (Camb)., 2004, vol. 23, p. 2778-2779. Go to original source... Go to PubMed...
    7. COZZOLINO, R. - PALLADINO, P. - ROSSI, F., et al. Antineoplastic cyclic astin analogues kill tumour cells via caspase-mediated induction of apoptosis. Carcinogenesis, 2005, vol. 26, no. 4, p. 733-739. Go to original source... Go to PubMed...
    8. DILIP de SILVA, E. - WILLIAMS, DE. - ANDERSEN, RJ., et al. Motuporin, a potent protein phosphatase inhibitor isolated from the Papua New Guinea sponge Theonella swinhoei gray. Tetrahedron Lett., 1992, vol. 33, no. 12, p. 1561-1564. Go to original source...
    9. DUAN, RD. - CHENG, Y. - ERLANSON-AALBERTSSON, C. Effect of emeriamine on exocrine and endocrine pancreatic function in normal and diabetic rats. Scand. J. Clin. Lab. Invest., 1992, vol. 52, no. 7, p. 579-584. Go to original source... Go to PubMed...
    10. GUGNANI, HC. - VIJAVAN, VK. - TYAGI, P., et al. Onychomycosis due to Emericella quadrilineata. J. Clin. Microbiol., 2004, vol. 42, no. 2, p. 914-916. Go to original source... Go to PubMed...
    11. GUILLOU, Y. - ROBIN, Y. Phascoline (N-(3-Guanidinopropionyl)-2-hydroxy-n-heptylamine) and phascolosomine (N-(3-Guanidinoisobutyryl)-2-methoxy-n-heptylamine), Two new guanidino compounds from sipunculid worms. Isolation and structure. J. Biol. Chem., 1973, vol. 248, no. 16, p. 5668-5672. Go to original source...
    12. GUO, YW. - TRIVELLONE, E. New Hurghamids from a Red Sea sponge of the genus Hippospongia. J. Asian Nat. Prod. Res., 2000, vol. 2, no. 4, p. 251-256. Go to original source... Go to PubMed...
    13. HOLZINGER, A. Jasplakinolide: An Actin-Specific Reagent that Promotes Actin Polymerization. Methods Mol. Biol., 2009, vol. 586, p. 71-87. Go to original source... Go to PubMed...
    14. HOURDOU, ML. - BESSON, F. - TENOUX, I., et al. Fatty acid and beta-amino acid syntheses in strains of Bacillus subtilis producing iturinic antibiotics. Lipids, 1989, vol. 24, no. 11, p. 940-944. Go to original source... Go to PubMed...
    15. CHIDECKEL, EW. - FEDAN, JS. - MIKE, P. Polyamines and putreanine relax respiratory tract smooth muscle in the guinea-pig. Eur. J. Pharmacol., 1985, vol. 116, no. 1/2, p. 187-190. Go to original source... Go to PubMed...
    16. JUARISTI, E. - SOLOSHONOK, VA. Enantioselective synthesis of beta-amino acids. 2nd Ed. Wiley Intersci., 2005. 634 p. Go to original source...
    17. KAKIMOTO, Y. - NAKAJIMA, T. - KUMON, A., et al. Putreanine, N-(4-aminobutyl)-3-aminopropionic acid. An amino acid occurring uniquely in the mammalian central nervous system. J. Biol. Chem., 1969, vol. 244, no. 21, p. 6003-6007. Go to original source...
    18. KOBAYASHI, S. - KOBAYASHI, J. - YAZAKI, R., et al. Toward the total synthesis of onchidin, a cytotoxic cyclic depsipeptide from a mollusc. Chem. Asian J., 2007, vol. 2, no. 1, p. 135-144. Go to original source... Go to PubMed...
    19. LAMBEIN, F. - KUO, YH. - KUSAMA-EGUCHI, K., et al. 3-N-oxalyl-L-2,3-diaminopropanoic acid, a multifunctional plant metabolite of toxic reputation. ARKIVOC, 2007, vol. 9, p. 45-52. Go to original source...
    20. LELAIS, G. - SEEBACH, D. β2-Amino acids - Syntheses, occurrence in natural products, and components of β-peptides. Biopolymers (Peptide Science), 2004, vol. 76, p. 206-243. Go to original source... Go to PubMed...
    21. MÁTLOVÁ, J. - KRAJČÍ, V. - PATOČKA, J. Toxiny sinic (cyanotoxiny) a jejich účinek na lidské zdraví. Kontakt, 2004, roč. 6, č. 1, s. 43-51.
    22. MAYNES, JT. - LUU, HA. - CHERNEY, MM., et al. Crystal structures of protein phosphatase-1 bound to motuporin and dihydromicrocystin-LA: elucidation of the mechanism of enzyme inhibition by cyanobacterial toxins. J. Mol. Biol., 2006, vol. 356, no. 1, p. 111-120. Go to original source... Go to PubMed...
    23. MORIMOTO, K. - SHIMADA, N. - NAGANWA, H., et al. The structure of antrimycin. J. Antibiot., 1981, vol. 34, no. 12, p. 1615-1618. Go to original source... Go to PubMed...
    24. MORITA, H. - NAGASHIMA, S. - TAKEYA, K., et al. Astins A and B, antitumor cyclic pentapeptides from Aster tataricus. Chem. Pharm. Bull. (Tokyo), 1993, vol. 41, no. 5, p. 992-993. Go to original source... Go to PubMed...
    25. MORITA, H. - NAGASHIMA, S. - TAKEYA, K., et al. Solution forms of antitumor cyclic pentapeptides with 3,4-dichlorinated proline residues, astins A and C, from Aster tataricus. Chem. Pharm. Bull. (Tokyo), 1995, vol. 43, no. 8, p. 1395-1397. Go to original source... Go to PubMed...
    26. NAKAO, Y. - MATSUNAGA, S. - FUSETANI, N. Three more cyclotheonamides, C, D, and E, potent thrombin inhibitors from the marine sponge Theonella swinhoei. Bioorg. Med. Chem., 1995, vol. 3, no. 8, p. 1115-1122. Go to original source... Go to PubMed...
    27. NEEMAN, I. 2-Methylene-beta-alanine methyl ester: a toxic amino acid originating from the sponge Fasciospongia cavernosa. Arch. Toxicol. (Suppl.), 1983, vol. 6, p. 258-260. Go to original source... Go to PubMed...
    28. PATOČKA, J. - KUEHN, GD. Natural polyamines and their biological consequence in mammals. Acta Medica (Hradec Kralove), 2000, vol. 43, no. 4, p. 119-124. Go to original source...
    29. PATOČKA, J. Smrtící cyanobakterie a jejich toxiny. Bull. ČSBMB, 2008, vol. 28, p. 21-23.
    30. PATOČKA, J. - STŘEDA, L. Protein biotoxins of military significance. Acta Medica (Hradec Kralove), 2006, vol. 49, no. 1, p. 3-11. Go to original source...
    31. PERRY, TL. - HANSEN, S. - KLOSTER, M. Occurrence of putreanine in human brain. J. Neurochem., 1972, vol. 19, no. 5, p. 1395-1396. Go to original source... Go to PubMed...
    32. RODRÍGUEZ, JU. - FERNÁNDEZ, R. - QUINOÁ, E., et al. Onchidin: A cytotoxic depsipeptide with C2 symmetry from a marine mollusc. Tetrahedron Lett., 1994, vol. 35, no. 49, p. 9239-9242. Go to original source...
    33. SALIBA, KJ. - KIRK, K. CJ-15,801, a fungal natural product, inhibits the intraerythrocytic stage of Plasmodium falciparum in vitro via an effect on pantothenic acid utilisation. Mol. Biochem. Parasitol., 2005, vol. 141, no. 1, p. 129-131. Go to original source... Go to PubMed...
    34. SANO, T. - KAYA, K. A 3-amino-10-chloro-2-hydroxydecanoic acid-containing tetrapeptide from Oscillatoria agardhii. Phytochemistry, 1997, vol. 44, no. 8, p. 1503-1505. Go to original source...
    35. SEILER, N. - KNODGEN, B. - GITTOS, MW., et al. On the formation of amino acids deriving from spermidine and spermine. Biochem. J., 1981, vol. 200, no. 1, p. 123-132. Go to original source... Go to PubMed...
    36. SHIH, C. - TEICHER, BA. Cryptophycins: a novel class of potent antimitotic antitumor depsipeptides. Curr. Pharm. Des., 2001, vol. 7, no. 13, p. 1259-1276. Go to original source... Go to PubMed...
    37. SHINAGAWA, S. - KANAMARU, T. - HARADA, S., et al. Chemistry of emeriamine and its analogs and their inhibitory activity in long-chain fatty acid oxidation. J. Med. Chem., 1987, vol. 30, no. 8, p. 1458-1463. Go to original source... Go to PubMed...
    38. SKROPENA, D. Deep-sea natural products. Nat. Prod. Rep., 2008, vol. 25, p. 1131-1166. Go to original source... Go to PubMed...
    39. SPITELLER, P. - RÜTH, M. - NUSSBAUM, F. von, et al. Detection of a 2,3-aminomutase in the mushroom Cortinarius violaceus This contribution was supported by the Deutsche Forschungsgemeinschaft (SFB 369). Angew. Chem. Int. Ed. Engl., 2000, vol. 39, no. 15, p. 2754-2756. Go to original source...
    40. SUGIE, Y. - DEKKER, KA. - HIRAI, H., et al. CJ-15,801, a novel antibiotic from a fungus, Seimatosporium sp. J. Antibiot. (Tokyo), 2001, vol. 54, no. 12, p. 1060-1065. Go to original source... Go to PubMed...
    41. TAN, LT. Bioactive natural products from marine cyanobacteria for drug discovery. Phytochemistry, 2007, vol. 68, no. 7, p. 954-979. Go to original source... Go to PubMed...
    42. TAN, LT. - SITACHITTA, N. - GERWICK, WH. The guineamides, novel cyclic depsipeptides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula. J. Nat. Prod., 2003, vol. 66, no. 6, p. 764-771. Go to original source... Go to PubMed...
    43. TESTA, E. - FONTANELLA, L. - CRISTIANI, GF. Substances active on the central nervous system. IV. Derivatives of 2-ethyl-2-phenyl-beta-alanine. Il Farmaco Sci., 1958, vol. 13, no. 6, p. 437-446. Go to PubMed...
    44. VERWEIJ, PE. - VARGA, J. - HOUBRAKEN, J., et al. Emericella quadrilineata as cause of invasive aspergillosis. Emerg. Infect. Dis., 2008, vol. 14, no. 4, p. 566-572. Go to original source... Go to PubMed...
    45. WILLIAMS, PG. - YOSHIDA, WY. - QUON, MK., et al. Ulongapeptin, a cytotoxic cyclic depsipeptide from a Palauan marine cyanobacterium Lyngbya sp. J. Nat. Prod., 2003, vol. 66, no. 5, p. 651-654. Go to original source... Go to PubMed...

    Return to the content