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[ CAS No. 3061-90-3 ] {[proInfo.proName]}

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Chemical Structure| 3061-90-3
Chemical Structure| 3061-90-3
Structure of 3061-90-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3061-90-3 ]

CAS No. :3061-90-3 MDL No. :MFCD00066031
Formula : C12H16N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :OMNVYXHOSHNURL-WPRPVWTQSA-N
M.W : 236.27 Pubchem ID :96814
Synonyms :
L-Alanyl-L-phenylalanine;H-Ala-Phe-OH;NSC 89630;Ala-phe

Safety of [ 3061-90-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3061-90-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3061-90-3 ]

[ 3061-90-3 ] Synthesis Path-Downstream   1~58

  • 3
  • [ 605-65-2 ]
  • [ 3061-90-3 ]
  • [ 134423-82-8 ]
YieldReaction ConditionsOperation in experiment
48%
  • 4
  • [ 3061-90-3 ]
  • [ 79410-44-9 ]
YieldReaction ConditionsOperation in experiment
36.8% With sodium hydroxide; (C8H17)3NMeCl; triflic azide In dichloromethane Ambient temperature;
  • 5
  • [ 1738-73-4 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In water; acetic acid; <i>tert</i>-butyl alcohol Yield given;
  • 6
  • [ 18979-06-1 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
With water at 30℃; Peptidamidase aus dem Flavedo von Orangen; Yield given;
  • 7
  • [ 103-72-0 ]
  • [ 121574-54-7 ]
  • [ 3061-90-3 ]
  • (S)-2-Acetylamino-N-((S)-6-oxo-2-phenylamino-5,6-dihydro-4H-[1,3]thiazin-5-yl)-propionamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethylmorpholine;; acetic acid In ethanol at 37℃; for 2.5h; other reagents, other times, other temp.;
  • 8
  • [ 121574-46-7 ]
  • [ 3061-90-3 ]
  • (S)-2-Acetylamino-N-((S)-2-oxo-pyrrolidin-3-yl)-propionamide [ No CAS ]
  • [ 121574-70-7 ]
YieldReaction ConditionsOperation in experiment
With NaHCO3 buffer at 60℃; for 96h; other buffers, other peptides, transpeptidation extent, pH dependence;
  • 9
  • [ 105995-30-0 ]
  • [ 3061-90-3 ]
  • (S)-2-{(S)-2-[(S)-5-((S)-2-Acetylamino-propionylamino)-2-amino-5-oxo-pentanoylamino]-propionylamino}-3-phenyl-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 60℃; for 96h; 0.25 M NaHCO3 buffer;
  • 10
  • [ 3061-90-3 ]
  • [ 84700-44-7 ]
  • [ 78-84-2 ]
  • (S)-2-[(S)-2-(1-Cyano-2-methyl-propylamino)-propionylamino]-3-phenyl-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In methanol for 48h;
  • 11
  • [ 100431-45-6 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
With bis-(trifluoroacetoxy)-iodo-benzene In water; acetonitrile for 3h;
  • 12
  • [ 3061-90-3 ]
  • [ 100-51-6 ]
  • [ 1738-73-4 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid In benzene Heating;
  • 13
  • [ 14533-84-7 ]
  • [ 3061-90-3 ]
  • (S)-3-Phenyl-2-[(S)-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-propionic acid pentafluorophenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With pyridine In N,N-dimethyl-formamide Ambient temperature;
  • 14
  • (S)-2-{(S)-2-[((S)-5-Oxo-pyrrolidine-2-carbonyl)-amino]-propionylamino}-3-phenyl-propionic acid [ No CAS ]
  • [ 3061-90-3 ]
  • EAF [ No CAS ]
YieldReaction ConditionsOperation in experiment
With methanesulfonic acid at 60℃; for 3h; var. temp., var. time, var. MSA concentration, other pyroglutamyl peptides;
  • 15
  • [ 3061-90-3 ]
  • [ 98-88-4 ]
  • benzoyl-L-alanyl-L-phenylalanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide; sodium carbonate In 1,4-dioxane for 5h;
  • 16
  • [ 3061-90-3 ]
  • Bz-Gly-Pro-OMe [ No CAS ]
  • [ 56672-76-5 ]
  • (S)-2-((S)-2-[(S)-1-(2-Benzoylamino-acetyl)-pyrrolidine-2-carbonyl]-amino}-propionylamino)-3-phenyl-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With borate buffer; prolyl endopeptidase from Flavobacterium meningoseptum; sodium chloride In water at 37℃; partition factor p determination;
YieldReaction ConditionsOperation in experiment
katalyt. Hydrolyse: k(i);
der Hydrolyse durch Co(trien)(OH)(H2O)2+ (Tab.1);
  • 18
  • trans-chrotonyl chloride [ No CAS ]
  • [ 3061-90-3 ]
  • (S)-2-[(S)-2-((E)-But-2-enoylamino)-propionylamino]-3-phenyl-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide at 20℃; for 3h;
  • 19
  • [ 3061-90-3 ]
  • [ 102-92-1 ]
  • (S,S)-2-[2-(3-phenyl-2-propenoylamino)propanoylamino]-3-phenylpropionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide at 20℃; for 3h;
  • 20
  • [ 3061-90-3 ]
  • [ 51908-29-3 ]
  • (S)-3-Phenyl-2-{(S)-2-[3-(4-sulfamoyl-phenyl)-thioureido]-propionylamino}-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetone Heating;
  • 21
  • pGlu-Lys-Ala-Phe-OH [ No CAS ]
  • [ 63-91-2 ]
  • [ 3061-90-3 ]
  • H-Lys-Ala-Phe-OH [ No CAS ]
  • H-Glu-Lys-Ala-Phe-OH [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride at 60℃; for 2h;
  • 22
  • [ 3061-90-3 ]
  • 4-[(adamant-1-yl)methylenoxycarbonyl]phthalic anhydride [ No CAS ]
  • 2-[(S)-1-((S)-1-Carboxy-2-phenyl-ethylcarbamoyl)-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid adamantan-1-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
30%
  • 23
  • [ 2543-29-5 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In methanol for 24h;
0.26 g (100%) In ethanol XX.B L-Alanyl-L-Phenylalanine (Via Full Protection Procedure) B. A mixture of N-benzyloxycarbonyl-L-alanyl-L-phenylalanine benzyl ester (0.50 g, 1.1 mmol) and 10% Pd palladium on carbon (0.1 g) in ethyl alcohol (150 mL) was shaken on a Parr hydrogenation apparatus for 6.5 h at 20° C. The reaction mixture was filtered and the filtrate rinsed with water (100 mL). The solution was concentrated to give 0.26 g (100%) of L-alanyl-L-phenylalanine. HPLC analysis showed >99% purity and no evidence of racemization.
0.26 g (100%) In ethanol XXI.B L-Alanyl-L-Phenylalanine (Via Full Protection Procedure) B. A mixture of N-benzyloxycarbonyl-L-alanyl-L-phenylalanine benzyl ester (0.50 g, 1.1 mmol) and 10% Pd palladium on carbon (0.1 g) in ethyl alcohol (150 mL) was shaken in a Parr hydrogenation apparatus for 6.5 h at 20° C. The reaction mixture was filtered and the filtrate rinsed with water (100 mL). The solution was concentrated to give 0.26 g (100%) of L-alanyl-L-phenylalanine. HPLC analysis showed >99% purity and no evidence of racemization.
  • 24
  • [ 3061-90-3 ]
  • [ 77-76-9 ]
  • L-alanyl-L-phenylalanine methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride at 20℃;
  • 25
  • [ 25172-67-2 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Z-Ala-O-COO-isoBu; (S)-Phe ester salt With 4-methyl-morpholine In dichloromethane at -15 - 20℃; Stage #2: With hydrogen In methanol for 24h; Further stages.;
  • 26
  • [ 3061-90-3 ]
  • [ 952312-44-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. HCl / 20 °C 2: dimethylformamide / -10 - 20 °C
  • 27
  • [ 3061-90-3 ]
  • C51H56N2O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aq. HCl / 20 °C 2: dimethylformamide / -10 - 20 °C 3: 76 percent / substituted Grubbs-type ruthenium carbene complex / CH2Cl2 / 18 h / 40 °C
  • 28
  • [ 1738-78-9 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 4 h / 20 °C 2: H2 / Pd / acetic acid; 2-methyl-propan-2-ol; H2O
  • 29
  • [ 16874-17-2 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 97 percent / triethylamine, 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / CHCl3; tetrahydrofuran / Ambient temperature 2: 80 percent / 1N aq. NaOH / ethanol / 2 h / Ambient temperature 3: 82 percent / N-hydroxysuccinimide, N,N'-dicyclohexylcarbodiimide, NH3 / tetrahydrofuran / Ambient temperature 4: TFA / CH2Cl2 / 3 h / 0 - 20 °C 5: <bis(trifluoroacetoxy)iodo>benzene / acetonitrile; H2O / 3 h
  • 30
  • [ 100431-52-5 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 82 percent / N-hydroxysuccinimide, N,N'-dicyclohexylcarbodiimide, NH3 / tetrahydrofuran / Ambient temperature 2: TFA / CH2Cl2 / 3 h / 0 - 20 °C 3: <bis(trifluoroacetoxy)iodo>benzene / acetonitrile; H2O / 3 h
  • 31
  • [ 100431-53-6 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 3 h / 0 - 20 °C 2: <bis(trifluoroacetoxy)iodo>benzene / acetonitrile; H2O / 3 h
  • 32
  • [ 100431-51-4 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 80 percent / 1N aq. NaOH / ethanol / 2 h / Ambient temperature 2: 82 percent / N-hydroxysuccinimide, N,N'-dicyclohexylcarbodiimide, NH3 / tetrahydrofuran / Ambient temperature 3: TFA / CH2Cl2 / 3 h / 0 - 20 °C 4: <bis(trifluoroacetoxy)iodo>benzene / acetonitrile; H2O / 3 h
  • 33
  • [ 3061-90-3 ]
  • (S)-2-[(S)-2-(1-Carbamoyl-2-methyl-propylamino)-propionylamino]-3-phenyl-propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: AcOH / methanol / 48 h 2: HCl / 4 h / 0 °C
  • 34
  • [ 3061-90-3 ]
  • [ 84759-79-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AcOH / methanol / 48 h 2: HCl / 4 h / 0 °C 3: Amberlyst 15 acid resin / 48 h / Heating
YieldReaction ConditionsOperation in experiment
10.c b) c) conversion to NH2 --CO-Ala-Phe 30 mg of PhOC-Ala-Phe are dissolved in 0.5 ml of a 1:1 mixture by volume of concentrated ammonium hydroxide (25%) and MeOH. After 3 hours, HPLC analysis indicates a complete and selective conversion (by-products <2%). The reaction medium is diluted with THF until the mixture becomes turbid. After overnight storage in a refrigerator, a theoretical quantity of NH2 -CO-Ala-Phe is recovered in the form of an ammonium salt by filtration. α: 33.1 (c=O,4/H2 O) HPLC: tR =10.14 min NMR (1 H) in DMSO-d6:
0.122 g (92%) XXI.B L-Alanyl-L-Phenylalanine (Via Partial Protection Procedure) B. A mixture of N-benzyloxycarbonyl-L-alanyl-L-phenylalanine (0.208 g, 0.562 mmol) and 10% Pd on carbon (0.1 g) in 95% ethyl alcohol (50 mL) was shaken on a Parr hydrogenation apparatus for 16 h at 20° C. The reaction mixture was filtered and the filtrate rinsed with water (100 mL). The combined solutions were concentrated to give 0.122 g (92%) of L-alanyl-L-phenylalanine as a white solid. HPLC analysis showed >99.5% purity and no evidence of racemization.
0.122 g (92%) XXII.B L-Alanyl-L-Phenylalanine (Via Partial Protection Procedure) B. A mixture of N-benzyloxycarbonyl-L-alanyl-L-phenylalanine (0.208 g, 0.562 mmol) and 10% Pd on carbon (0.1 g) in 95% ethyl alcohol (50 mL) was shaken on a Parr hydrogenation apparatus for 16 h at 20° C. The reaction mixture was filtered and the filtrate rinsed with water (100 mL). The combined solutions were concentrated to give 0.122 g (92%) of L-alanyl-L-phenylalanine as a white solid. HPLC analysis showed >99.5% purity and no evidence of racemization.
  • 36
  • [ 3061-90-3 ]
  • [ 4502-00-5 ]
  • N-(1-carboxy-3-methylbutyl)-L-alanyl-L-phenylalanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
197 mg (88.7%) With sodium cyanoborohydride In water 11 N-(1-Carboxy-3-methylbutyl)-L-alanyl-L-phenylalanine EXAMPLE 11 N-(1-Carboxy-3-methylbutyl)-L-alanyl-L-phenylalanine A solution of L-alanyl-L-phenylalanine (150 mg) and 4-methyl-2-oxopentanoic acid sodium salt (483 mg) in water was adjusted to pH 7 and treated with 120 mg of sodium cyanoborohydride at room temperature for several days. The reaction was quenched with Dowex 50 (H+), added to a column of the same resin and eluted with 2% pyridine in water. Freeze drying yielded 197 mg (88.7%) of white fluffy solid. N-(1-carboxy-3-methylbutyl)-L-alanyl-L-phenylalanine. Mass spectrum showed peaks at 551 for the trisilyl derivative minus methyl (566-15), 479 for the disilyl derivative minus methyl (494-15), and 449 for the trisilyl derivative minus--COOTMS (566-117). The nmr spectrum showed broad doublets at 0.95 and 1.5 ppm, complex weak absorption in the 2.8--3.4 ppm range, and a singlet at 7.1 ppm.
  • 37
  • copper(II) carbonate [ No CAS ]
  • [ 3061-90-3 ]
  • Cu(dipeptide of L-alanine and L-phenylalanine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water byproducts: CO2; dipeptide dissolved in small amt. of distd. water, CuCO3 added to this soln. in slight excess over 1:1 stoichiometry under stirring until CO2 evolution ceased; filtered, concd. at 80°C, filtered, washed with water-acetone mixt. (1:1), elem. anal.;
  • 38
  • bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] [ No CAS ]
  • [ 3061-90-3 ]
  • (C5(CH3)5)IrCl(NH2CH(CH3)C(O)NCH(CH2C6H5)CO2H) [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With NaOMe In methanol inert atmosphere; stirring for 5 h; evapn., stirring with CHCl3, sepn. from ppt., crystn. on layering with pentane, drying (vac.); elem. anal.;
  • 39
  • gold(III) tetrachloride trihydrate [ No CAS ]
  • [ 3061-90-3 ]
  • Au(alanylphenylalanyl(1-))Cl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In water soln. of HAuCl4*3H2O in H2O added to aq. soln. of ligand, 2 wk; ppt. filtered, washed with H2O, dried over P2O5; elem. anal.;
  • 40
  • [ 3061-90-3 ]
  • [ 322474-21-5 ]
  • [ 1262797-20-5 ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: L-alanyl-L-phenylalanine With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: N,N'-bis-Boc-S-methyl-isothiourea With dmap In N,N-dimethyl-formamide at 20℃;
  • 41
  • [ 31010-69-2 ]
  • [ 3061-90-3 ]
  • C19H19N7O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol; dimethyl sulfoxide at 80℃;
  • 42
  • [ 3061-90-3 ]
  • C17H24BNO2*ClH [ No CAS ]
  • C29H38BN3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃;
  • 43
  • [ 3061-90-3 ]
  • C18H26BNO2*ClH [ No CAS ]
  • C30H40BN3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃;
  • 44
  • [ 7524-50-7 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 0.25 h / 0 °C 1.2: 24 h / 20 °C 2.1: sodium hydroxide / methanol / 10 h 3.1: trifluoroacetic acid / 2 h / 20 °C
Multi-step reaction with 3 steps 1: thermolysin / aq. acetate buffer / 6 h / 50 °C / pH 6 / Enzymatic reaction 2: immobilized bovine α-chymotrypsin on silica coated magnetite nanoparticles / acetonitrile; aq. phosphate buffer / 2 h / 37 °C / pH 8 / Green chemistry; Enzymatic reaction 3: hydrogen / methanol / 2 h / 27 °C / 750.08 Torr / Green chemistry
  • 45
  • (S)-2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylpropanoic acid [ No CAS ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid at 20℃; for 2h;
  • 46
  • [ 3061-90-3 ]
  • [ 63-91-2 ]
YieldReaction ConditionsOperation in experiment
With leucine aminopeptidase In aq. phosphate buffer; water Enzymatic reaction;
  • 47
  • [ 66-71-7 ]
  • copper(ll) sulfate pentahydrate [ No CAS ]
  • [ 3061-90-3 ]
  • [Cu(Ala-Phe)(phen)]*4H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In ethanol; water at 50 - 60℃; 2.1 Synthesis of the complexes and analytical characterization General procedure: Ternary Cu-dipeptide-phenanthroline complexes where L-dipeptide: Gly-Val, Ala-Gly, Ala-Phe, Phe-Ala, Phe-Val or Phe-Phe were obtained as follows: 0.1 mmol of dipeptide was dissolved in the appropriate volume of warm water (50-200 mL) and 0.1 mmol of CuSO4·5H2O was added. The pH was adjusted to 7 with a NaOH solution. A solution of 0.1 mmol of phen in 10 mL of ethanol was added. The compounds were isolated by evaporation at 50-60°C, until blue crystals were formed. Yield 60-80%. To obtain adequate single crystals, a small amount of the solution was allowed to slowly evaporate at room temperature. Blue-purple crystals were obtained for [Cu(Ala-Phe)(phen)]·4H2O, [Cu(Phe-Phe)(phen)]·3H2O and [Cu(Phe-Ala)(phen)]·4H2O, and green ones for [Cu(Phe-Val)(phen)]·4.5H2O.
  • 48
  • [ 3061-90-3 ]
  • [ 56-41-7 ]
  • [ 63-91-2 ]
YieldReaction ConditionsOperation in experiment
With L-leucine aminopeptidase In aq. buffer at 37℃; Enzymatic reaction;
  • 49
  • [ 2768-53-8 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In methanol at 27℃; for 2h; Green chemistry;
  • 50
  • tetrabutylphosphonium phenylalanine salt [ No CAS ]
  • [ 2491-20-5 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
70 %Chromat. Stage #1: tetrabutylphosphonium phenylalanine salt; L-alanine methyl ester hydrochloride at 60℃; for 6h; Inert atmosphere; Stage #2: With acetic acid In chloroform at 20℃; for 3h;
  • 51
  • [ 3061-90-3 ]
  • Se-phenyl (2S)-2-[(tert-butoxycarbonyl)amino]propaneselenoate [ No CAS ]
  • [ 56133-10-9 ]
YieldReaction ConditionsOperation in experiment
73% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6h;
  • 52
  • [ 3061-90-3 ]
  • [ 2224-52-4 ]
  • [ 26698-64-6 ]
  • 53
  • [ 63-91-2 ]
  • [ 2224-52-4 ]
  • [ 3061-90-3 ]
  • [ 26698-64-6 ]
  • 54
  • [ 484-11-7 ]
  • [ 3061-90-3 ]
  • [ 7732-18-5 ]
  • C26H26CuN4O3*4H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In ethanol 2.1 Synthesis of the complexes and analytical characterization General procedure: Heteroleptic Cu-dipeptide-necuproine complexes where L-dipeptide: Gly-Val, Gly-Leu, Gly-Phe, Ala-Gly, Ala-Phe, Val-Phe, Phe-Ala or Phe-Phe were obtained as follows (Fig. 1). 0.1mmol of dipeptide were dissolved in the minimum volume of warm water (10-50mL) and 0.1mmol of CuSO4·5H2O was added. The pH was adjusted to 7 with a 0.1M NaOH solution. A solution of 0.1mmol of neo in 5mL of ethanol was added, while stirring. The compounds were isolated by evaporation at 40-50°C, until blue crystals were formed. Yield 60-70%. Crystals suitable for X-ray analysis were obtained by slow evaporation of solvent at room temperature.
  • 55
  • [ 3061-90-3 ]
  • antiparallel (Cys-Phe-Cys)<SUB>2</SUB> [ No CAS ]
  • C30H38N6O8S4*C12H16N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In aq. phosphate buffer ITC measurements General procedure: For determination of binding constants ITC was measured in phosphate buffered solutions (pH 7.4, 100 mM). Concentration were used as noted. In general, the titrant concentration was 20 times the concentration of the other peptide. ITC was performedon a Nano ITC low volume titration calorimeter (TA Instruments) with a cell volume of 170 μL. The program used 20 injections of 2.5 μL each in an interval of 2.5 min and a stirring rate of 350 rpm. The device was operated using ITC Run version 2.1.7.0 (TA Instruments). For each experiment a correction for the dilution was measured by titrating the titrant to pure solvent. For initial analysis of the heat rates NanoAnalyze version 3.8.0 (TA Instruments) was used. Data fits and thermodynamic data was obtained using a numerical approximation using Microsoft Excel.
  • 56
  • [ 35661-39-3 ]
  • [ 35661-40-6 ]
  • [ 3061-90-3 ]
YieldReaction ConditionsOperation in experiment
7% Stage #1: N-Fmoc L-Phe With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 1.08333h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine Further stages; 1.1 Solid-phase peptide synthesis (SPPS) General procedure: 1.1.1. Loading of the resin (PS 1)Loading of the resin was performed under an atmosphere of argon. The according amino acid (1.5 equiv relative to resin loading) was dissolved in dry DCM and a small amount of DMF (synthesis grade) and was added to 2-chlorotrityl-resin (1.6 mmol/g resin). After addition of DIPEA (2 equiv relative to resin loading) the mixture was agitated by a stream of argon for 5 min. Following another addition of DIPEA (3 equiv relative to resin loading), agitation was continued for 1 h. The remaining reactive groups were quenched with MeOH p.a. (1 mL/g resin) for 15 min. After filtration of the resin it was washed consecutively with DCM p.a. (3 × 20 mL), DMF p.a. (3 × 20 mL), DCM p.a. (3 × 20 mL) and MeOH p.a. (3 × 20 mL) and was dried until weight constant was reached. 1.1.2. Manual synthesis (PS 2A). Dry beads prepared as described in PS 1 were swollen in DMF p.a. for 45 min by shaking the reaction vessel. After sucking of the DMF p.a. the Fmoc-group was cleaved with 20% piperidine in DMF for 20 min. The resin was washed with DMF p.a. (4 times) and alternately with DCM p.a. (3 times) and isopropanol p.a. (3 times). The success of cleavage was controlled by the Kaiser test. Equal amounts of 5% ninhydrin in EtOH, 80% phenol in EtOH and 0.001 M KCN in pyridine were mixed with a few beads and heated for 1 min to 100 °C. A blue color indicated free amine functions on the resin. 1.1.4. Cleavage from resin and removal from permanent protecting groups (PS3). Cleavage of the resin and removal of permanent protection groups was performed according to common literature procedures. Prior to splitting of the peptide from the resin, the N-terminal Fmoc-group has to be removed by treatment with 20% piperidine in DMF for 20 min. After washing with DMF p.a. (4 times) and alternately with DCM (2 times) and isopropanol p.a. (2 times), the beads were suspended in a solution of TFA/H2O/EDT/TIS = 94:2.5:2.5:1 and stirred for 8 h at room temperature. After filtration, the beads were washed with TFA (5 times) and the filtrate was concentrated until the peptide started to precipitate. Addition of cold Et2O resulted in complete precipitation and the suspension was kept overnight in the freezer. The peptide was collected by filtration, washed with Et2O and dried in high vacuum to yield the peptides as white, hygroscopic crude products which were stored under argon.
  • 57
  • C30H38N6O8S4*C12H16N2O3 [ No CAS ]
  • [ 3061-90-3 ]
  • antiparallel (Cys-Phe-Cys)<SUB>2</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
In aq. phosphate buffer ITC measurements General procedure: For determination of binding constants ITC was measured in phosphate buffered solutions (pH 7.4, 100 mM). Concentration were used as noted. In general, the titrant concentration was 20 times the concentration of the other peptide. ITC was performedon a Nano ITC low volume titration calorimeter (TA Instruments) with a cell volume of 170 μL. The program used 20 injections of 2.5 μL each in an interval of 2.5 min and a stirring rate of 350 rpm. The device was operated using ITC Run version 2.1.7.0 (TA Instruments). For each experiment a correction for the dilution was measured by titrating the titrant to pure solvent. For initial analysis of the heat rates NanoAnalyze version 3.8.0 (TA Instruments) was used. Data fits and thermodynamic data was obtained using a numerical approximation using Microsoft Excel.
  • 58
  • copper(II) carbonate [ No CAS ]
  • [ 3061-90-3 ]
  • [ 7732-18-5 ]
  • C12H20CuN2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 60 - 80℃; for 1h; [Cu(dipeptide)(tmp)] complexes General procedure: A solution of [Cu(dipeptide)] precursor with general formula[Cu(dipeptide)] was firstly obtained by dissolving thecorresponding dipeptide in the minimum volume of H2O.To this solution, a 50% excess of CuCO3was added andstirred at 60-80 °C for 1 h. The CuCO3that was not solubilizedwas filtered off. The resulting blue solution wasevaporated at 60-80 °C until an adequate amount of solidis obtained which was then filtered off, washed with coldH2Oand air dried, as described by Facchin et al. [23]. Theadequate amount of solid (0.1 mmol) was dissolved in hotH2Oto make 50 mL of a 2 mM, solution (0.1 mmol). Itwas mixed under stirring at 60 °C with 10 mL of a 0.01 Methanolic solution of tmp (0.1 mmol). The dipeptidesused were: Gly-Gly, l-Gly-Phe, l-Ala-Gly, l-Ala-Phe, l-Val-Phe, l-Phe-Ala, and l-Phe-Phe. In all cases a darkblue-green solid was obtained after evaporation at 25 °C.Yield: 50-70%. Figure 1 presents a scheme of the syntheticprocedure and of the proposed coordination of thecomplexes. Blue prismatic crystals were obtained for[Cu(Gly-Gly)(tmp)]·6H2O by recrystallization in 95%ethanol. Recrystallization tests for the remaining ternarycomplexes were unsuccessful.The obtained solids correspond to the general formula[Cu(l-dipeptide)(tmp)]·xCH3CH2OHxH2O, where thedipeptide acts as a - 2 anion, making neutral complexesof the following formulas and elemental compositions.[Cu(Gly-Gly)(tmp)]·6H2O C1 Calc. for C20H34CuN4O9/Found: %C: 44.64/44.68, %N: 10.41/10.25, %H: 6.36/6.20;[Cu(l-Gly-Phe)(tmp)]·CH3CH2OH·2H2O C2 Calc./Found(C29H38CuN4O6) %C: 57.84/57.39, %N: 9.30/8.96, %H:6.36/5.90; [Cu(l-Ala-Gly)(tmp)]·3.5H2O C3 Calc./Found(C21H31CuN4O6.5) %C: 49.75/49.75, %N: 11.05/11.12,%H: 6.16/5.99; [Cu(l-Ala-Phe)(tmp)]·3H2O C4 Calc./Found (C28H36CuN4O6) %C: 57.18/57.52, %N: 9.52/9.40,%H: 6.17/6.07; [Cu(l-Val-Phe)(tmp)]·CH3CH2OH C5Calc./Found (C32H40CuN4O4) %C: 63.19/63.58, %N:9.21/8.79, %H: 6.62/6.15; [Cu(l-Phe-Ala)(tmp)]·3.5H2OC6 Calc./Found (C28H37CuN4O6.5) %C: 56.31/56.15, %N:9.38/9.29, %H: 6.24/6.34; [Cu(l-Phe-Phe)(tmp)]·2H2OC7 Calc./Found (C34H38CuN4O5) %C: 63.19/63.60, %N:8.67/8.59, %H: 5.93/5.74. Only complexes C1, C3 and C4are soluble in water to mM concentrations, all the complexesare soluble in DMSO and DMSO/water mixtures.
at 60 - 80℃; for 1h; [Cu(dipeptide)(tmp)] complexes General procedure: A solution of [Cu(dipeptide)] precursor with general formula[Cu(dipeptide)] was firstly obtained by dissolving thecorresponding dipeptide in the minimum volume of H2O.To this solution, a 50% excess of CuCO3was added andstirred at 60-80 °C for 1 h. The CuCO3that was not solubilizedwas filtered off. The resulting blue solution wasevaporated at 60-80 °C until an adequate amount of solidis obtained which was then filtered off, washed with coldH2Oand air dried, as described by Facchin et al. [23]. Theadequate amount of solid (0.1 mmol) was dissolved in hotH2Oto make 50 mL of a 2 mM, solution (0.1 mmol). Itwas mixed under stirring at 60 °C with 10 mL of a 0.01 Methanolic solution of tmp (0.1 mmol). The dipeptidesused were: Gly-Gly, l-Gly-Phe, l-Ala-Gly, l-Ala-Phe, l-Val-Phe, l-Phe-Ala, and l-Phe-Phe. In all cases a darkblue-green solid was obtained after evaporation at 25 °C.Yield: 50-70%. Figure 1 presents a scheme of the syntheticprocedure and of the proposed coordination of thecomplexes. Blue prismatic crystals were obtained for[Cu(Gly-Gly)(tmp)]·6H2O by recrystallization in 95%ethanol. Recrystallization tests for the remaining ternarycomplexes were unsuccessful.The obtained solids correspond to the general formula[Cu(l-dipeptide)(tmp)]·xCH3CH2OHxH2O, where thedipeptide acts as a - 2 anion, making neutral complexesof the following formulas and elemental compositions.[Cu(Gly-Gly)(tmp)]·6H2O C1 Calc. for C20H34CuN4O9/Found: %C: 44.64/44.68, %N: 10.41/10.25, %H: 6.36/6.20;[Cu(l-Gly-Phe)(tmp)]·CH3CH2OH·2H2O C2 Calc./Found(C29H38CuN4O6) %C: 57.84/57.39, %N: 9.30/8.96, %H:6.36/5.90; [Cu(l-Ala-Gly)(tmp)]·3.5H2O C3 Calc./Found(C21H31CuN4O6.5) %C: 49.75/49.75, %N: 11.05/11.12,%H: 6.16/5.99; [Cu(l-Ala-Phe)(tmp)]·3H2O C4 Calc./Found (C28H36CuN4O6) %C: 57.18/57.52, %N: 9.52/9.40,%H: 6.17/6.07; [Cu(l-Val-Phe)(tmp)]·CH3CH2OH C5Calc./Found (C32H40CuN4O4) %C: 63.19/63.58, %N:9.21/8.79, %H: 6.62/6.15; [Cu(l-Phe-Ala)(tmp)]·3.5H2OC6 Calc./Found (C28H37CuN4O6.5) %C: 56.31/56.15, %N:9.38/9.29, %H: 6.24/6.34; [Cu(l-Phe-Phe)(tmp)]·2H2OC7 Calc./Found (C34H38CuN4O5) %C: 63.19/63.60, %N:8.67/8.59, %H: 5.93/5.74. Only complexes C1, C3 and C4are soluble in water to mM concentrations, all the complexesare soluble in DMSO and DMSO/water mixtures.
Same Skeleton Products
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