Metallkomplexe von Biologisch Wichtigen Liganden, CXLVIII [1]. Katalytische Peptidsynthese aus Glycinester miit Hilfe von Triflaten Und Cloriden der Seltenen Erden, sowie von Metall(III), (IV), (V) und (VI)-Chloriden / Metal Complexes of Biologically Important Ligands, CXLVIII [1]. Synthesis of Peptides from Glycine Ester Catalysed by Triflates and Chlorides of Metal(III, IV, V And VI) Ions

2003 ◽  
Vol 58 (1) ◽  
pp. 85-91 ◽  
Author(s):  
Jan Schapp ◽  
Wolfgang Beck
Keyword(s):  
Amino Acid ◽  
Metal Complexes ◽  
Dansyl Chloride ◽  
Amino Acid Esters ◽  
Metal Chlorides ◽  
Peptide Formation ◽  
Metal Triflates ◽  
High Yields ◽  
Acid Esters

Abstract Formation of di- and triglycine ethylester which were determined by HPLC after derivatisation with dansyl chloride was observed in medium to high yields from CH2Cl2 solutions of glycine ethylester in the presence of metal triflates and metal chlorides: FeCl3 (yield 82%), AlCl3 (73%), GdCl3 (56%), La(OTf)3 (59%), Sc(OTf)3 (55%), ZrCl4 (62%), HfCl4 (60%), VOCl3 (43%), TaCl5 (29%). Esters of higher α-amino acid esters (AlaOMe, PheOMe) gave lower yields in peptide formation.

Metallkomplexe mit biologisch wichtigen Liganden, CXV. Addition von α-Aminosäureestern an [CpFe(CO)3]+: Carbamoylkomplexe Cp(OC)2Fe-C(O)NHCHRCO2R’ und Kristallstruktur von Cp(OC)2Fe-C(O)NHCH2CO2Et / Metal Complexes of Biologically Important Ligands, CXV. Addition of α-Amino Acid Esters to [CpFe(CO)3]+: Carbamoyl Complexes Cp(OC)2Fe-C(O)NHCHRCO2R' and Crystal Structure of Cp(OC)2Fe-C(O)NHCH2CO2Et

1999 ◽  
Vol 54 (3) ◽  
pp. 385-388 ◽  
Author(s):  
Reinhold Urban ◽  
Kurt Polbom ◽  
Wolfgang Beck
Keyword(s):  
Crystal Structure ◽  
Amino Acid ◽  
Metal Complexes ◽  
Amino Acid Esters ◽  
X Ray Diffraction ◽  
Carbonyl Ligand ◽  
X Ray ◽  
Acid Esters

α-Amino acid esters can be added to a carbonyl ligand of [CpFe(CO)3]+CF3SO3- to give the carbamoyl complexes Cp(OC)2Fe-C(O)NHCHRCO2R′ (R = H, Me, CHMe2, CH2Ph; R′ = Et, Me). This type of reaction may be useful for the marking of peptides at the amino end. The crystal structure of Cp(OC)2Fe-C(O)NHCH2CO2Et was determined by X-ray diffraction.

Synthesis and infrared spectra of some transition metal complexes of α-amino acid esters

1967 ◽  
Vol 20 (4) ◽  
pp. 675 ◽  
Author(s):  
RW Hay ◽  
LJ Porter
Keyword(s):  
Amino Acid ◽  
Transition Metal ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Infrared Spectra ◽  
Metal Ion ◽  
Amino Acid Esters ◽  
Visible Spectra ◽  
Metal Ratio ◽  
Acid Esters

A variety of transition metal complexes of a-amino acid esters have been synthesized, and characterized by analysis, conductivity measurements, and infrared spectra. The complexes can be broadly divided into two groups: (a) complexes in which only a metal-nitrogen bond occurs with the α-amino group of the ester, and (b) complexes in which chelate ring formation occurs via secondary donor groups on the ligand. These latter complexes are found with methyl L-histidinate, methyl γ-glutamate, and methyl L-cysteinate. With the exception of a methyl tryptophanate complex, the infrared spectra show that there is no interaction between the carbonyl group of the ester and the metal ion. The visible spectra of aqueous solutions of the esters and copper(II) at a ligand/metal ratio of 5 : 1 have maxima in the 600-650 mμ range at pH 7 consistent with copper-nitrogen bonding only.

Metal complexes of biologically important ligands, LXXVIII. Synthesis of palladium complexes of ferrocenyl-substituted amino acid derivatives

1995 ◽  
Vol 73 (7) ◽  
pp. 1164-1174 ◽  
Author(s):  
Doris Freiesleben ◽  
Kurt Polborn ◽  
Christian Robl ◽  
Karlheinz Sünkel ◽  
Wolfgang Beck
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Metal Complexes ◽  
Palladium Complexes ◽  
Amino Acid Derivatives ◽  
Amino Acid Esters ◽  
X Ray Diffraction ◽  
Chelate Complexes ◽  
X Ray ◽  
Acid Esters

Schiff bases from ferrocene aldehyde and α-amino acidates react with PdCl2 or Na2PdCl4 to give N,O-chelate complexes (2a–e, 3). The related N-ferrocenylmethylen-α-amino acid esters give, with Pd(OAc)2, cyclopalladated acetate-bridged complexes (4a,b). N,O-chelate complexes (5–7) are obtained from Na2PdCl4 with N-ferrocenylmethyl prolinate and-alaninate as well as with N,N-dibenzyl glycinate. The ethyl ester of N,N-dibenzylglycine and Pd(OAc)2 form the cyclopalladated acetate-bridged complex 8, while the ester of N-monobenzylglycine and Na2PdCl4 affords trans-PdCl2(L)2 with a monodentate N-coordinated ligand. The structures of 2a, 4a, 5, 7, and 9 were determined by X-ray diffraction. Keywords: ferrocene, amino acids, palladium(II) complexes, crystal structures.

Metallkomplexe von biologisch wichtigen Liganden, CVI [1]. Metallkomplexe von Donor-substituierten Oxazolin-5-onen sowie von Bis(oxazolin-5-onen) / Metal Complexes of Biologically Important Ligands CVI [1], Metal Complexes of Donor Substituted Oxazolones and of Bis(oxazolones)

1998 ◽  
Vol 53 (9) ◽  
pp. 965-972 ◽  
Author(s):  
Markus Prem ◽  
Werner Bauer ◽  
Kurt Polbom ◽  
Wolfgang Beck
Keyword(s):  
Amino Acid ◽  
Metal Complexes ◽  
Nucleophilic Addition ◽  
Metal Salts ◽  
Amino Acid Esters ◽  
X Ray Diffraction ◽  
Chelate Complexes ◽  
X Ray ◽  
Close Proximity ◽  
Acid Esters

A series of chelate complexes 1-12 of Cu(II), Ni(II), Pd(II), and Ru(III) with the anion of 2-(2′-hydroxyphenyl)-5(4H)-oxazolone and with 2-(2′-aminophenyl)-5(4H)-oxazolone were prepared from metal salts or from chloro-bridged complexes [(R3P)MCl2]2 (M = Pd, Pt) and [(p-cymene)RuCl2]2. Nucleophilic addition of α-amino acid esters to the bis-chelate complexes M(oxophenyloxazolone)2(M = Ni, Cu) gave the dipeptide derivatives 13-18. Dinuclear Pd(II) and Pt(II) chelate complexes 19-23 were obtained from phenylene- and ethylenebridged bis(oxazolones). The structures of (Et3P)(Cl)Pd(O,N-oxophenyloxazolone) (6) and of Cl2(Et3P)Pt(2,2′-phenylene-bis(4-methyloxazolone)Pt(PEt3)Cl2 (20) were determined by X-ray diffraction. In complex 20 a close proximity of two phenylene H atoms to the metal is observed.

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