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.

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.

Metal Complexes of Biologically Important Ligands, CLXIX [1]. Palladium(II) and Platinum(II) N,O-Chelate Complexes (R3P)(Cl)M(α-aminoacidate) with the Anions of Serine, Threonine, 3,4-Dehydroproline and 4-Hydroxyproline

2008 ◽  
Vol 63 (2) ◽  
pp. 124-128 ◽  
Author(s):  
Elfriede Schuhmann ◽  
Wolfgang Beck
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Metal Complexes ◽  
Nmr Spectra ◽  
Palladium Complexes ◽  
Chelate Complexes ◽  
Potassium Salts ◽  
Single Isomer ◽  
C Nmr

The N,O-chelates M(3,4-dehydro-D,L-prolinate)2 (M = Ni, Cu) have been obtained from Ni(OH)2 or Cu(OH)2 and the amino acid. The complexes (R3P)(Cl)M(α-aminoacidate) (M= Pd, Pt) have been synthesized from the chloro bridged compounds (R3P)(Cl)M(μ-Cl)2M(PR3)Cl (M = Pd, Pt; R = Et, n-Bu, Ph) and the potassium salts of the α-amino acids D,L-serine, D,L-threonine, 3,4-dehydro-D,Lproline and 4-hydroxy-L-proline. According to the 31P NMR and 13C NMR spectra the complexes with serinate and threoninate are formed as mixtures of cis/trans N-M-P isomers, whereas for the palladium complexes with 3,4-dehydroprolinate and 4-hydroxyprolinate a single isomer is observed

Metallkomplexe mit biologisch wichtigen Liganden, LXXXIV [1] Halbsandwich-Komplexe von Rhodium(III), Iridium(III), Cobalt(III), Ruthenium(II), Ruthenium(III) und Chrom(III) mit Aminosäureester-Liganden Metal Complexes with Biologically Important Ligands, LXXXIV [1] Half-Sandwich Complexes o f Rhodium(III), Iridium(III), Cobalt(III), Ruthenium(II), Ruthenium(III) and Chromium(III) with Amino Acid Ester Ligands

1996 ◽  
Vol 51 (2) ◽  
pp. 187-200 ◽  
Author(s):  
Ralph Bergs ◽  
Roland Krämer ◽  
Michael Maurus ◽  
Bernhard Schreiner ◽  
Reinhold Urban ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Ester ◽  
Amino Acid Esters ◽  
Ethoxy Group ◽  
Exchange Reactions ◽  
Chelate Complexes ◽  
X Ray ◽  
Ester Exchange ◽  
Half Sandwich ◽  
Acid Esters

Abstract A series of cyclopentadienyl and pentamethylcyclopentadienyl complexes of cobalt, rhodium, iridium, ruthenium and chromium with a-amino-acid esters (L) as ligands was prepared and characterized: Cp*(Cl)2M(L) (1, 2: M = Rh, Ir), Cp(I)2Co(L) (4), [Cp(Ph3P)2Ru(L)]+BF- (6), [Cp(OC)(Ph3P)Ru]+BF- (7) and the paramagnetic compounds Cp*(Cl)2Ru(L) (8) and Cp(Br)2Cr(L) (9). AlaOMe and HisOMe form N ,O and N,N chelate complexes [Cp*(Cl)M(alaOMe)]+BF-4 (3: M = Rh, Ir), [Cp(I)Co(hisOMe)]+BF4. Cp*Co(CO)I2 and GlyOMe gave the N,O-dipeptide ester complex Cp*(I)Co(glyglyOMe)]+BF-4 (5). The crystal structures of Cp(I)2Co(glyOEt) and Cp*(Cl)2Ru(alaOMe) were determined by X-ray diffrac­tion. The complexes 1 and 2 undergo ester exchange reactions with CD3OD. [Cp*MCl2]2 (M = Rh, Ir) catalyze the exchange of the ethoxy group in Me2NCH2CO2Et by CD3OD.

Metallkomplexe mit biologisch wichtigen Liganden, CIV [1]. ortho-Palladierte Komplexe von N,N-Dimethyl-C-phenyl-glycinmethylester. Synthese von α-Aminosäure-Derivaten durch Insertion von Isocyaniden, CO, Alkenen und Alkinen in die Pd-C-Bindung / Metal Complexes of Biologically Important Ligands, CIV [ 1]. ortho-Palladated Complexes of N,N-Dimethyl-C-phenylglycine-methylester. Synthesis of α-Amino Acid Derivatives by Insertion of Isocyanides, CO, Alkenes, and Alkynes into the Pd-C Bond

1998 ◽  
Vol 53 (4) ◽  
pp. 448-458 ◽  
Author(s):  
Andreas Böhm ◽  
Kurt Polborn ◽  
Karlheinz Sünkel ◽  
Wolfgang Beck
Keyword(s):  
Acetic Acid ◽  
Amino Acid ◽  
Metal Complexes ◽  
Crystal Structures ◽  
Trinuclear Complex ◽  
Amino Acid Derivatives ◽  
X Ray Diffraction ◽  
X Ray ◽  
Derivatives Of ◽  
Amine Ligand

Abstract N,N-Dimethyl-C-phenylglycinemethylester reacts with Pd(OAc)2 in acetic acid to give the orthopalladated, acetato bridged complex 1. Treatment of 1 with sodium halide affords the chloro, bromo, and iodo bridged compounds [Me2NC(H)(CO2Me)C6H4PdX]2 (2a -c) (X = halide). From 2a and 1,1′-bis(diphenylphosphino)ferrocene the phosphine bridged trinuclear complex 3 is obtained. Substitution of the amine ligand of 2a by the phosphino group is observed for the reaction of 2a with Ph2PC(Me)C(Me)PPh2. Insertion of 2,6-dimethyl-phenylisocyanide, CO, alkyl-vinyl-ketones, and diphenylacetylene into the Pd-C bond o f 2a -c provides the orthosubstituted organic and organometallic derivatives of phenylglycine 6a -c, 7, 8a -b and 9a -c. The crystal structures of 1, 4a, 6a, 7 and 9a were determined by X-ray diffraction.

Metallkomplexe mit biologisch wichtigen Liganden, CIX [1]. Metallorganische Verbindungen von Platin(II), Ruthenium(II), Rhodium (III) und Iridium (III) mit Oxocarbonyl-N-geschützten a-Am inosäuren und L-Methionylglycinat / Metal Complexes with Biologically Important Ligands, CIX [1]. Organometallic Compounds of Platinum(II), Ruthenium(II), Rhodium(III), and Iridium(III) with Oxocarbonyl-N-protected a-Amino Acids and L-Methionylglycinate

1998 ◽  
Vol 53 (12) ◽  
pp. 1501-1505 ◽  
Author(s):  
Markus Prem ◽  
Kurt Polbom ◽  
Wolfgang Beck
Keyword(s):  
Amino Acids ◽  
Metal Complexes ◽  
Diffraction Analysis ◽  
Chelate Ring ◽  
Organometallic Compounds ◽  
Chelate Complex ◽  
X Ray Diffraction ◽  
Chelate Complexes ◽  
Proton Abstraction ◽  
X Ray

Abstract The reaction of cis-(Ph3P)2PtCl2 with BOC-N-glycine and FMOC-N-alanine gives the carboxylate coordinated complexes cis-(Ph3P)2 Pt(Cl)(O2CCH2NHBOC) (1) and cis- (Ph3 P)2Pt(Cl)(O2CC(H)(Me)NHFMOC (2). Chloride and proton abstraction from 1 affords the N,O-chelate complex (Ph3P)2Pt(O2CCH2NBOC) (3). From the chloro-bridged compounds [Cp*MCl2]2 (M = Rh, Ir), [(p-cymene)RuCl2]2 and BOC-N-L-MetGlyOH (L) the compounds Cp*M(Cl)2L (4, 5) and (p-cymene)Ru(Cl)2L (6 ) with the mono-dentate dipeptide are obtained which in the presence of NaOMe form O,N,S-bis(chelate) complexes 7 - 9 . The X-ray diffraction analysis of the iridium O,N,S chelate complex 8 shows a five membered and a seven membered chelate ring.

Metal Complexes of Biologically Important Ligands, CLXXIV [1]. Palladium(II) and Platinum(II) Complexes with Schiff Bases from 2-(Diphenylphosphino)benzaldehyde and α-Amino Acid Esters

2010 ◽  
Vol 65 (4) ◽  
pp. 503-510 ◽  
Author(s):  
Bernhard Schreiner ◽  
Christian Robl ◽  
Barbara Wagner-Schuh ◽  
Wolfgang Beck
Keyword(s):  
Schiff Base ◽  
Amino Acid ◽  
Schiff Bases ◽  
Ester Group ◽  
Amino Acid Esters ◽  
X Ray Diffraction ◽  
Tridentate Ligands ◽  
X Ray ◽  
Reduced Schiff Base ◽  
Acid Esters

A series of palladium(II) and platinum(II) complexes Cl2M(P-N-O) (M = Pd, Pt) with bidentate Schiff bases (P-N-O) from 2-(diphenylphosphino)benzaldehyde and α-amino acid esters has been synthesized, using PdCl2 or K[PtCl3(C2H4)], respectively. Abstraction of chloride from Cl2M(P-N-O) (using AgBF4) has afforded the cationic complexes [(P-N-O)M(Cl)]+BF4− in which the Schiff bases function as tridentate ligands with coordination of the ester group. The structures of Cl2Pd(Ph2PC6H4C(H)=N-CH2CO2Et) and of [(Cl)Pd(Ph2PC6H4C(H)=NC(H)(CH2CH=CH2)CO2Me)]+BF4− have been determined by X-ray diffraction. Complexes (L)MCl2 and [(L)MCl]+BF4 (M = Pd, Pt) have also been prepared with the reduced Schiff base Ph2PC6H4CH2NHC(H)(CH2Ph)CO2Me.

Metal Complexes of Biologically Important Ligands, CLXXV [1]. Pentamethylcyclopentadienyl Halfsandwich Complexes of Rhodium(III) and Iridium(III) with Schiff Bases from 2-(Diphenylphosphino)- benzaldehyde and α-Amino Acid Esters

2010 ◽  
Vol 65 (6) ◽  
pp. 679-686 ◽  
Author(s):  
Bernhard Schreiner ◽  
Barbara Wagner-Schuh ◽  
Wolfgang Beck
Keyword(s):  
Schiff Base ◽  
Amino Acid ◽  
Schiff Bases ◽  
Ester Group ◽  
Tridentate Ligand ◽  
Molar Ratio ◽  
Amino Acid Esters ◽  
X Ray Diffraction ◽  
X Ray ◽  
Acid Esters

The reactions of the chlorido-bridged complexes [Cp*M(Cl)(μ-Cl)]2 (M = Rh, Ir) with Schiff bases (P-N-O) from 2-(diphenylphosphino)benzaldehyde and α-amino acid esters afford the complexes Cp*M(Cl)2(P-N-O) in which the ligands function as monodentate P donors (M = Ir) or as bidentate P-N donors (M = Rh). These complexes can be converted into cationic complexes [Cp*M(Cl)(P-NO)]+ with bidentate P-N ligands by treatment with NH4PF6. The cationic complexes [Cp*M(Cl)(PN- O)]+Cl− have been detected also in solutions of Cp*M(Cl)2(P-N-O). The P-N-coordinated complex [Cp*Rh(Cl)(Ph2P-C6H4-C(H)=N-C(H)(CH2Ph)CO2Me)]+PF6− was characterized by X-ray diffraction. From Cp*M(Cl)2(P-N-O) and AgBF4 or AgPF6 (molar ratio 1 : 2) the dicationic complexes [Cp*M(P-N-O)]2+ are formed in which the ester group is also coordinated to the metal atom. The Schiff base from 2-(diphenylphosphino)benzaldehyde and allylglycine ester acts as a tridentate ligand, however with coordination of the C=C allyl group instead of the ester function.

Enzyme–substrate interactions promote the self-assembly of amino acid derivatives into supramolecular hydrogels

2016 ◽  
Vol 4 (5) ◽  
pp. 844-851 ◽  
Author(s):  
Yanyan Xie ◽  
Renliang Huang ◽  
Wei Qi ◽  
Yuefei Wang ◽  
Rongxin Su ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Self Assembly ◽  
The Self ◽  
Amino Acid Derivatives ◽  
Amino Acid Esters ◽  
Substrate Interactions ◽  
Substrate Interaction ◽  
Enzyme Substrate ◽  
Acid Esters

The first example of enzyme-substrate interaction-promoted self-assembly was reported for the synthesis of supramolecular hydrogels from Fmoc-amino acids and amino acid esters in the presence of α-chymotrypsin.

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