ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
α-Amino Ketones - A Contribution to the Synthesis of Optically Active Derivatives of Amino Acids and PeptidesThe synthesis of N-Z-protected methyl ketonesDie Nomenklatur der Ketonderivate von Aminosäuren und Peptiden entspricht den IUPACIUB Nomenclature Recommendations 1983, Eur. J. Biochem. 138 (1984) 9. Um die Beziehung zu den Aminosäuren herzustellen, wird für Aminoaceton die Bezeichnung Glycylmethan GlyCH3 benutzt.Weitere verwendete Abkürzungen: Z- = Benzyloxycarbonyl-, E = Ether, PE = Petrolether, EE = Essigsäureethylester, CABE = Chlorameisensäure-i-butylester, TEA = Triethylamin, DMAP = 4-Dimethyl-aminopyridin, HMDS = Hexamethyldisiloxan, TMS = Tetramethylsilan, TRH = Thyreotropin Releasing Hormon, MSH-RIF (MIF) = MSH-Release-Inhibiting-Factor (MSH = Melanocyten stimulierendes Hormon). from amino acids via the chloromethyl ketones and dehalogenation of the latter with zinc in glacial acetic acid is described. Deprotection of the methyl ketones results in the formation of hydrohalogenides of the α-aminoalkyl methyl ketones further converted to N-acylated peptide ketones as analogs of peptide hormones or as competitively acting substrate analogs of proteolytic enzymes. Aminoacetone is conveniently prepared as well as methyl-pyrrolidyl ketone and methyl-piperidyl ketone.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19863280410
Permalink