Incorporation of the tricarbonylchromium ligand in aqueous media on the side chain of aromatic amino-acids

Sergheraert, Christian; Brunet, J.-C.; Tartar, André

doi:10.1039/c39820001417

Cited by 16 publications

(3 citation statements)

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“…The preferred method for the synthesis of (arene)Cr(CO) 3 complexes is thermolysis of Cr(CO) 6 under an inert atmosphere (N 2 or Ar) in the presence of an excess of the arene in a high-boiling solvent. This can be the arene itself or a variety of solvent mixtures, − the most frequently adopted procedure is a mixture of the arene, dibutyl ether, and THF . This procedure is suited for the preparation of a wide range of complexes, often in high yields (80−95%) with reaction times typically in the 1−4 day range.…”

Section: Complexation Methodsmentioning

confidence: 99%

Transition-Metal-Mediated Dearomatization Reactions

2000

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Section: Complexation Methodsmentioning

confidence: 99%

Transition-Metal-Mediated Dearomatization Reactions

2000

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“…Conjugates of biomolecules such as amino acids and peptides with covalently bound organometallic compounds have recently gained considerable attention. − In functional conjugates, the unique properties of the organometallic entity are exploited for the sensitive detection of the biomolecule . For instance, a technique for monitoring the level of drugs such as phenobarbital in human blood using infrared spectroscopy has been developed for clinical applications in Jaouen's group and the name Carbonylmetalloimmunoassay (CMIA) has been coined. , In this assay, the standard procedure is the reaction of an activated organometallic acid with a primary amino group of the biomolecule like, for instance, phenobarbital.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Alkynyl Amino Acids and Peptides and Their Palladium-Catalyzed Coupling to Ferrocene

1999

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A method for attaching organometallics to the C-terminus of amino acids via a Pd-catalyzed two-step procedure is presented. Boc-protected enantiomerically pure amino acids 1 (a Phe, b Leu, c Met, d Ser) are reacted with 1,1-diethylpropargylamine to yield alkynyl amino acids 2. After reaction with (p-iodoanilido)ferrocene carboxylic acid 3 in the presence of 5 mol % PdCl2(PPh3)2/CuI ferrocene amino acids 4 are obtained in ca. 80% yield. The reaction does not require anhydrous conditions and tolerates functional groups such as amides, alcohols (Ser, 4d) or thioethers (Met, 4c). A complete characterization by multinuclear NMR (including 15N) is carried out. Cyclic voltammetry shows a reversible wave at about +190 mV (vs Fc/Fc+) independent of the nature of the attached amino acid. In the solid state, 2a forms a left-handed helix along the crystallographic c axis which is stabilized by hydrogen bonds as revealed by a single-crystal X-ray structure determination. A comparison of IR data in solution and the solid state suggests that hydrogen bonding is also important for the solid-state structures of ferrocene amino acids 4 but does not play a role in solution. The use of this methodology for peptide chemistry is demonstrated by labeling the dipeptide Boc-Met-Phe-OH at the C-terminus and the tripeptide Boc-Phe-Glu-Leu-OMe with ferrocene. The alkyne anchoring group in the tripeptide is introduced at the Cγ(Glu) atom at an early stage of the peptide synthesis and is not affected by subsequent deprotection and coupling reactions.

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“…B. P henylala nin) m it geschützten Carboxyl-und A m inogrup pen reagieren mit H exacarbonylchrom zu Tricarbonyl-K om plexen des Typs (O C )3Cr(776-C6H 5R ) [18]. D erivate des 2-(3-Thienyl)glycins sollten sich ü b er ihr heteroarom atisches ^-System ebenfalls an M etallcarbonylfragm ente koordinieren lassen (vgl.…”

Section: Etallorganische Komplexe M It N-geschiitztem 2-(3-thienyl)unclassified

Metallkomplexe mit biologisch wichtigen Liganden, LXXIV [1]. Metallorganische Verbindungen von 2-(3-Thienyl)glycin und dessen Derivaten / Metal Complexes with Biologically Important Ligands, LXXIV [1]. Organometallic Compounds of 2-(3-Thienyl)glycine and Derivatives thereof

Schuhmann

Robl

Beck

1994

Zeitschrift Für Naturforschung B

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N.O-Chelate complexes of R,S-2-(3-thienyl)glycinate (L) have been obtained: ML2 (M = Ni, Cu), (n-Bu3P)(Cl)M(L) (M = Pd. Pt), (η3-C3H5)Pd(L), C6H4CH,CHNMe2Pd(L), (η6-p-cymene)(Cl)Ru(L), (η5-C5Me5)(Cl)M(L) (M = Rh, Ir) and (η5-C5H5)(OC)2Mo(L). The methyl ester of R,S-2-(3-thienvl)glycine (L') forms the complexes trans-CT2PdL′2, cis- Cl2Pt(L')2, (η-Bu3P)(Cl2)M(L') (M = Pd, Pt) and (η5-C5Me5)(Cl)2M(L') (M = Rh, Ir) in which the ligand L' is coordinated through the amino group. The structures of (η3-C3H5)Pd(L) and of (η5-C5Me5)(Cl2)Ir(L') have been determined by X-ray diffraction. N- Benzoyl-2-(3-thienylglycine methyl ester reacts with Cr(CO)6 to yield a tricarbonyl complex with an η6-coordinated phenyl group. N-Benzoyl-R,S-2-(3-thienyl)glycinate (L") and (η5- C5H5)2TiCl2 give the diastereoisomers [(η5-C5H5)2Ti(R-L")(R-L")2/(η5-C5H5)2Ti(S-L") (S-L")] and (η5-C5H5)2Ti(R-L")(S-L") with Ti-O-bonds.

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Incorporation of the tricarbonylchromium ligand in aqueous media on the side chain of aromatic amino-acids

Cited by 16 publications

References 0 publications

Transition-Metal-Mediated Dearomatization Reactions

Transition-Metal-Mediated Dearomatization Reactions

Synthesis of Alkynyl Amino Acids and Peptides and Their Palladium-Catalyzed Coupling to Ferrocene

Metallkomplexe mit biologisch wichtigen Liganden, LXXIV [1]. Metallorganische Verbindungen von 2-(3-Thienyl)glycin und dessen Derivaten / Metal Complexes with Biologically Important Ligands, LXXIV [1]. Organometallic Compounds of 2-(3-Thienyl)glycine and Derivatives thereof

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