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13485-59-1

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13485-59-1 Usage

Uses

L-Alanyl-L-proline is a dipeptide that contains a sterically constrained proline, a well-known turn inducer in proteins.

Definition

ChEBI: A dipeptide composed of L-alanine and L-proline joined by a peptide linkage.

Biochem/physiol Actions

Alanyl dipeptides such as ala-leu, ala-lys, ala-gly, ala-pro, ala-tyr and ala-phe may be used in physicochemical studies or to evaluate dipeptide separation technologies. Alanyl dipeptides may also be used for studying cell uptake mechanisms, dipeptide metabolism or cell growth supplementation benefits.

Check Digit Verification of cas no

The CAS Registry Mumber 13485-59-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,4,8 and 5 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 13485-59:
(7*1)+(6*3)+(5*4)+(4*8)+(3*5)+(2*5)+(1*9)=111
111 % 10 = 1
So 13485-59-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H14N2O3/c1-5(9)7(11)10-4-2-3-6(10)8(12)13/h5-6H,2-4,9H2,1H3,(H,12,13)

13485-59-1 Well-known Company Product Price

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  • TCI America

  • (A1495)  L-Alanyl-L-proline  >98.0%(T)

  • 13485-59-1

  • 5g

  • 1,520.00CNY

  • Detail

13485-59-1Synthetic route

N-benzyloxycarbonyl-L-alanyl-L-proline
21027-01-0

N-benzyloxycarbonyl-L-alanyl-L-proline

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
With acetic acid; 10% palladium on active carbon In methanol for 2h; Hydrogenation;98%
With hydrogen; palladium on activated charcoal In sodium hydroxide
(S)-1-((S)-2-Phosphonoamino-propionyl)-pyrrolidine-2-carboxylic acid
76166-63-7

(S)-1-((S)-2-Phosphonoamino-propionyl)-pyrrolidine-2-carboxylic acid

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
With sodium chloride at 37℃; Rate constant; pH=7.5;
L-proline
147-85-3

L-proline

L-alanine N-carboxyanhydride
2224-52-4

L-alanine N-carboxyanhydride

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
With potassium hydroxide; potassium carbonate In tetrahydrofuran; water at 5 - 10℃; for 0.25h;92 % Chromat.
N-tert-butoxycarbonyl-L-alanyl-L-proline
33300-72-0

N-tert-butoxycarbonyl-L-alanyl-L-proline

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
With methoxybenzene; trifluoroacetic acid
With hydrogenchloride In ethyl acetate
With trifluoroacetic acid In dichloromethane at 0℃; for 3h;
Multi-step reaction with 2 steps
1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 °C
2: tetra(n-butyl)ammonium hydroxide; water / methanol; tert-butyl methyl ether / 12 h
View Scheme
L-proline
147-85-3

L-proline

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: BOP; DIPEA / CH2Cl2
2: HCl / ethyl acetate
View Scheme
Multi-step reaction with 2 steps
2: TFA, anisole
View Scheme
L-proline ethyl ester monohydrochloride
33305-75-8

L-proline ethyl ester monohydrochloride

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 83 percent / ethyl acetate; dimethylformamide / 2 h / -10 - 20 °C
2: 85 percent / NaOH; HCl / methanol; CH2Cl2 / 3 h
3: 98 percent / acetic acid / 10 percent Pd/C / methanol / 2 h
View Scheme
N-carbobenzoxy-β-alanylproline ethyl ester

N-carbobenzoxy-β-alanylproline ethyl ester

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / NaOH; HCl / methanol; CH2Cl2 / 3 h
2: 98 percent / acetic acid / 10 percent Pd/C / methanol / 2 h
View Scheme
(naphth-1-yl)methylamine
118-31-0

(naphth-1-yl)methylamine

1-pyruvyl-L-proline
76391-12-3

1-pyruvyl-L-proline

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
With nitrogen; palladium In ethanol
With nitrogen; palladium In ethanol
1-pyruvyl-L-proline
76391-12-3

1-pyruvyl-L-proline

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
With hydrogenchloride; nitrogen; hydroxylamine hydrochloride; sodium acetate; palladium hydroxide-on-carbon In ethanol; water
With hydrogenchloride; nitrogen; hydroxylamine hydrochloride; sodium acetate; palladium hydroxide-on-carbon In ethanol; water
Fmoc-Ala-Pro-OH
186023-44-9

Fmoc-Ala-Pro-OH

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide for 0.5h;
methyl (2S)-pyrrolidine carboxylate
2577-48-2

methyl (2S)-pyrrolidine carboxylate

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / 0 °C
1.2: 24 h
2.1: lithium hydroxide / tetrahydrofuran; water / 5 h / 0 °C
3.1: trifluoroacetic acid / dichloromethane / 3 h / 0 °C
View Scheme
C16H30N2O5Si

C16H30N2O5Si

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide; water In methanol; tert-butyl methyl ether for 12h;
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-p-toluenesulfonyl-L-alanyl-L-proline

N-p-toluenesulfonyl-L-alanyl-L-proline

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; aqueous sodium hydroxide (10 ml)-dioxane; water95.8%
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

4-phenyl-butyric acid 4-guanidino-phenyl ester

4-phenyl-butyric acid 4-guanidino-phenyl ester

4-phenylbutanoyl-L-alanyl-L-proline

4-phenylbutanoyl-L-alanyl-L-proline

Conditions
ConditionsYield
With HEPES buffer; sodium chloride; calcium chloride; clostripain (EC 3.4.22.8) In water; N,N-dimethyl-formamide at 25℃; pH=8.0; Acylation;93%
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

3-benzoylamino-propionic acid 4-guanidino-phenyl ester

3-benzoylamino-propionic acid 4-guanidino-phenyl ester

Bz-β-Ala-Ala-Pro-OH

Bz-β-Ala-Ala-Pro-OH

Conditions
ConditionsYield
With HEPES buffer; sodium chloride; calcium chloride; clostripain (EC 3.4.22.8) In water; N,N-dimethyl-formamide at 25℃; pH=8.0; Acylation;91%
ethanol
64-17-5

ethanol

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

L-alanyl-L-proline ethyl ester hydrochloride
88098-06-0

L-alanyl-L-proline ethyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;90%
C27H33N9O9

C27H33N9O9

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

C29H42N10O9

C29H42N10O9

Conditions
ConditionsYield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 35℃; for 8h;81.39%
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

N-(pyrazinecarbonyl)glycine azide
117904-03-7

N-(pyrazinecarbonyl)glycine azide

N--L-alanyl>-L-proline

N--L-alanyl>-L-proline

Conditions
ConditionsYield
With sodium methylate In N,N-dimethyl-formamide for 70h; Ambient temperature;72%
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Ethyl 4-(β-indolyl)-2-ketobutyrate
79155-18-3

Ethyl 4-(β-indolyl)-2-ketobutyrate

N-[1-ethoxycarbonyl-3-(3-indolyl)propyl]-L-alanyl-L-proline
79155-17-2

N-[1-ethoxycarbonyl-3-(3-indolyl)propyl]-L-alanyl-L-proline

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 25℃; under 2068.6 Torr;70%
2-oxo-4-phenylbutanoic acid ethyl ester
64920-29-2

2-oxo-4-phenylbutanoic acid ethyl ester

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

enalapril
75847-73-3

enalapril

Conditions
ConditionsYield
With hydrogen In ethanol at 45℃; under 735.074 - 772.577 Torr; Catalytic behavior; Kinetics; Solvent; Reagent/catalyst;70%
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

(E)-ethyl-2-oxo-4-phenylbut-3-enoate
17451-20-6, 55674-14-1, 55629-96-4

(E)-ethyl-2-oxo-4-phenylbut-3-enoate

enalapril
75847-73-3

enalapril

Conditions
ConditionsYield
With 4 A molecular sieve; hydrogen; triethylamine; palladium In ethanol at 20℃; for 44h;65%
zinc(II) nitrate hexahydrate

zinc(II) nitrate hexahydrate

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

C16H26N4O6Zn

C16H26N4O6Zn

Conditions
ConditionsYield
In methanol for 1h;64%
copper(II) nitrate trihydrate

copper(II) nitrate trihydrate

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

C16H26CuN4O6

C16H26CuN4O6

Conditions
ConditionsYield
In methanol for 1h;62.35%
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

4-[1-(3-Nitro-pyridin-2-ylamino)-meth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one

4-[1-(3-Nitro-pyridin-2-ylamino)-meth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one

(S)-1-{(S)-2-[(Z)-2-Benzoylamino-3-(3-nitro-pyridin-2-ylamino)-acryloylamino]-propionyl}-pyrrolidine-2-carboxylic acid

(S)-1-{(S)-2-[(Z)-2-Benzoylamino-3-(3-nitro-pyridin-2-ylamino)-acryloylamino]-propionyl}-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water; acetonitrile for 2h; Heating;40%
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

2-phenyl-4-(5-ethoxycarbonyl-2-methylthio-4-pyrimidinylamino)methylene-5(4H)-oxazolone
124211-85-4

2-phenyl-4-(5-ethoxycarbonyl-2-methylthio-4-pyrimidinylamino)methylene-5(4H)-oxazolone

4-{(Z)-2-Benzoylamino-2-[(S)-2-((S)-2-carboxy-pyrrolidin-1-yl)-1-methyl-2-oxo-ethylcarbamoyl]-vinylamino}-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

4-{(Z)-2-Benzoylamino-2-[(S)-2-((S)-2-carboxy-pyrrolidin-1-yl)-1-methyl-2-oxo-ethylcarbamoyl]-vinylamino}-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium carbonate In water; acetonitrile for 2h; Heating;39%
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

2-phenyl-4-(4-chloro-6-methyl-2-pyrimidinylamino)methylene-5(4H)-oxazolone
124594-30-5

2-phenyl-4-(4-chloro-6-methyl-2-pyrimidinylamino)methylene-5(4H)-oxazolone

(S)-1-{(S)-2-[(Z)-2-Benzoylamino-3-(4-chloro-6-methyl-pyrimidin-2-ylamino)-acryloylamino]-propionyl}-pyrrolidine-2-carboxylic acid

(S)-1-{(S)-2-[(Z)-2-Benzoylamino-3-(4-chloro-6-methyl-pyrimidin-2-ylamino)-acryloylamino]-propionyl}-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate In water; acetonitrile for 2h; Heating;36%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

tert-butoxycarbonyl-D-prolinal
73365-02-3

tert-butoxycarbonyl-D-prolinal

C19H30N4O5

C19H30N4O5

Conditions
ConditionsYield
With ammonium chloride In methanol at 25℃; for 36h;36%
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

pyrrolidino[1,2-a]-2,6-diazacycloheptane-1,5-dione

pyrrolidino[1,2-a]-2,6-diazacycloheptane-1,5-dione

Conditions
ConditionsYield
In acetic anhydride for 2.5h; Cyclization; Heating;33%
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

potassium cyanide
151-50-8

potassium cyanide

(S)-1-[(S)-2-(1-Cyano-3-phenyl-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid
138247-41-3

(S)-1-[(S)-2-(1-Cyano-3-phenyl-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With acetic acid In methanol
4-phthalimidobutanal
3598-60-5

4-phthalimidobutanal

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

potassium cyanide
151-50-8

potassium cyanide

(S)-1-{(S)-2-[1-Cyano-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butylamino]-propionyl}-pyrrolidine-2-carboxylic acid

(S)-1-{(S)-2-[1-Cyano-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butylamino]-propionyl}-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With acetic acid In methanol for 48h;
3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

potassium cyanide
151-50-8

potassium cyanide

(S)-1-[(S)-2-(1-Cyano-3-methyl-but-2-enylamino)-propionyl]-pyrrolidine-2-carboxylic acid

(S)-1-[(S)-2-(1-Cyano-3-methyl-but-2-enylamino)-propionyl]-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With acetic acid In methanol for 48h;
2-(benzoylamino)acetaldehyde
6542-76-3

2-(benzoylamino)acetaldehyde

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

potassium cyanide
151-50-8

potassium cyanide

(S)-1-[(S)-2-(2-Benzoylamino-1-cyano-ethylamino)-propionyl]-pyrrolidine-2-carboxylic acid

(S)-1-[(S)-2-(2-Benzoylamino-1-cyano-ethylamino)-propionyl]-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With acetic acid In methanol for 48h;
In methanol for 72h;
N-tert.butyloxycarbonyl-alanine pentafluorophenyl ester
50903-48-5

N-tert.butyloxycarbonyl-alanine pentafluorophenyl ester

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

N-tert-butyloxycarbonyl-alanyl-alanyl-proline
63769-98-2

N-tert-butyloxycarbonyl-alanyl-alanyl-proline

Conditions
ConditionsYield
In 1,4-dioxane for 24h;
2-oxo-4-phenylbutanoic acid ethyl ester
64920-29-2

2-oxo-4-phenylbutanoic acid ethyl ester

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

A

enalapril
75847-73-3

enalapril

B

enalapril
76420-74-1

enalapril

Conditions
ConditionsYield
nickel Product distribution; var. catalysts and reducing agents, diastereomeric ratio;
With 3 A molecular sieve; hydrogen; nickel In ethanol at 23 - 28℃; under 2068.6 Torr; for 18h; Title compound not separated from byproducts;
With potassium fluoride; 3 A molecular sieve; hydrogen; acetic acid; nickel In ethanol at 22℃; under 760 Torr; for 18h; Yield given; Yields of byproduct given;
2-oxo-4-phenylbutanoic acid ethyl ester
64920-29-2

2-oxo-4-phenylbutanoic acid ethyl ester

L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

(S)-1-{(S)-2-[1-Ethoxycarbonyl-3-phenyl-prop-(E)-ylideneamino]-propionyl}-pyrrolidine-2-carboxylic acid
90414-32-7

(S)-1-{(S)-2-[1-Ethoxycarbonyl-3-phenyl-prop-(E)-ylideneamino]-propionyl}-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With 4 A molecular sieve In ethanol
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Boc-L-Pro-H
69610-41-9

Boc-L-Pro-H

potassium cyanide
151-50-8

potassium cyanide

C19H30N4O5

C19H30N4O5

Conditions
ConditionsYield
In methanol for 96h;
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

Boc-L-phenylalaninal
72155-45-4

Boc-L-phenylalaninal

potassium cyanide
151-50-8

potassium cyanide

(S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-1-cyano-3-phenyl-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid
94670-41-4, 94730-84-4

(S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-1-cyano-3-phenyl-propylamino)-propionyl]-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With acetic acid In methanol for 72h;
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

potassium cyanide
151-50-8

potassium cyanide

3-[(tert-butoxycarbonyl)amino]-4-phenylbutanaldehyde
130944-47-7

3-[(tert-butoxycarbonyl)amino]-4-phenylbutanaldehyde

(S)-1-[(S)-2-((S)-3-tert-Butoxycarbonylamino-1-cyano-4-phenyl-butylamino)-propionyl]-pyrrolidine-2-carboxylic acid

(S)-1-[(S)-2-((S)-3-tert-Butoxycarbonylamino-1-cyano-4-phenyl-butylamino)-propionyl]-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With acetic acid In methanol for 48h;
L-alanyl-L-proline
13485-59-1

L-alanyl-L-proline

potassium cyanide
151-50-8

potassium cyanide

(3S)-3-benzamido-4-phenylbutanal
94670-46-9

(3S)-3-benzamido-4-phenylbutanal

(S)-1-[(S)-2-((S)-3-Benzoylamino-1-cyano-4-phenyl-butylamino)-propionyl]-pyrrolidine-2-carboxylic acid

(S)-1-[(S)-2-((S)-3-Benzoylamino-1-cyano-4-phenyl-butylamino)-propionyl]-pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With acetic acid In methanol for 72h;

13485-59-1Relevant articles and documents

N -boc deprotection and isolation method for water-soluble zwitterionic compounds

Liu, Zhijian,Yasuda, Nobuyoshi,Simeone, Michael,Reamer, Robert A.

, p. 11792 - 11796 (2014)

A highly efficient TMSI-mediated deprotection and direct isolation method to obtain zwitterionic compounds from the corresponding N-Boc derivatives has been developed. This method has been demonstrated in the final deprotection/isolation of the β-lactamase inhibitor MK-7655 as a part of its manufacturing process. Further application of this process toward other zwitterionic compounds, such as dipeptides and tripeptides, has been successfully developed. Furthermore, a catalytic version of this transformation has been demonstrated in the presence of BSA or BSTFA.

Synthesis, characterization and in vitro DNA binding and cleavage studies of Cu(II)/Zn(II) dipeptide complexes

Arjmand, Farukh,Jamsheera,Mohapatra

, p. 75 - 85 (2013)

Novel dipeptide complexes Cu(II)?Val-Pro (1), Zn(II)?Val-Pro (2), Cu(II)?Ala-Pro (3) and Zn(II)?Ala-Pro (4) were synthesized and thoroughly characterized using different spectroscopic techniques including elemental analyses, IR, NMR, ESI-MS and molar conductance measurements. The solution stability study carried out by UV-vis absorption titration over a broad range of pH proved the stability of the complexes in solution. In vitro DNA binding studies of complexes 1-4 carried out employing absorption, fluorescence, circular dichroism and viscometric studies revealed the binding of complexes to DNA via groove binding. UV-vis titrations of 1-4 with mononucleotides of interest viz., 5′-GMP and 5′-TMP were also carried out. The DNA cleavage activity of the complexes 1 and 2 were ascertained by gel electrophoresis assay which revealed that the complexes are good DNA cleavage agents and the cleavage mechanism involved a hydrolytic pathway. Furthermore, in vitro antitumor activity of complex 1 was screened against human cancer cell lines of different histological origin.

Cyclo(l-proline-l-serine) Dipeptide Suppresses Seed Borne Fungal Pathogens of Rice: Altered Cellular Membrane Integrity of Fungal Hyphae and Seed Quality Benefits

Poonia, Baninderjit Kaur,Sidhu, Anjali,Sharma, Anju Bala

, p. 2160 - 2168 (2022/02/23)

Five proline-containing diketopiperazines (Pro-DKPs) produced by antagonistic microorganisms as secondary metabolites were selected and synthesized under laboratory conditions. Out of five synthesized Pro-DKPs, cyclo(l-Pro-l-Ser) (DKP-6) revealed the best inhibition of fungal pathogens (Fusarium verticillioides and Fusarium fujikuroi) of rice under in vitro conditions with effective doses lower than standard fungicide carbendazim. DKP-6 induced stress on the fungal cell membrane integrity, which was revealed by calcofluor white and propidium iodide assays, endorsed by ultra-microscopic details and soluble protein leakage assays. In vivo seed treatment of infested rice seeds with DKP-6 at 2000 μg/mL for 10 h of seed treatment inflicted best reduction in seed rot and seedling blight with respect to control and carbendazim. Significant enhancement in seedling quality parameters were also observed. The work presented the strong influence of cyclo(l-Pro-l-Ser) as a mycocidal seed treatment agent better than synthetic toxic fungicides for rice.

A process for preparing a renin - angiotensin - aldosterone system dual inhibitor compound of intermediate

-

Paragraph 0062; 0063; 0064; 0068; 0069; 0070, (2017/04/28)

The invention relates to an intermediate compound for preparing RAAS (renin-angiotensin-aldosterone system) dual inhibitor compounds. RAAS dual inhibitors can be used for treating diseases related to an RAAS such as high blood pressure and heart diseases.

For renin-angiotensin-aldosterone system dual inhibitor compounds

-

Paragraph 0077; 0078-0080, (2016/12/01)

The invention relates to a compound for a renin-angiotensin-aldosterone system dual inhibitor, which can be used for treating and blocking diseases related to an RAS system such as hypertension, congestive heart failure, pulmonary hypertension, renal insufficiency, renal ischemia, kidney failure, renal fibrosis, cardiac insufficiency, cardiomegaly, cardiac fibrosis, myocardial ischemia, cardiomyopathy, glomerulonephritis, renal colic, complication caused by diabetes such as nephropathy, vasculopathy, neuropathy, glaucoma, intraocular pressure elevation, atherosclerosis, restenosis after the arteries transluminal angioplasty, complication of blood vessels or cardiac surgical procedures, erectile dysfunction, hyperaldosteronism, lung fibrosis, scleroderma, anxiety, cognitive disorder, complication caused by the treatment of immunosuppressor and other diseases associated to the renin-angiotensin system.

RAAS system as a dual inhibitor compounds

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Paragraph 0051; 0052-0054, (2017/02/28)

The invention discloses a compound used as a dual inhibitor for RAAS (rennin angiotensin aldosterone system) and particularly relates to a compound shown in formula (I), a stereisomer thereof or a pharmaceutically acceptable salt thereof. The compound can be used for treating and blocking RAS-associated diseases such as hypertension and heart disease, can be used for preventing or treating hypertension, congestive heart failure, pulmonary hypertension, renal insufficiency, renal ischemia, kidney failure, renal fibrosis, cardiac insufficiency, cardiac hypertrophy, cardiac fibrosis, myocardial ischemia, cardiomyopathy, glomerulonephritis, renal colic, complications such as nephropathy caused by diabetes, vasculopathy, vasculopathy, glaucoma, intraocular pressure elevation, atherosis, restenosis after revascularization, complications after blood vessel or cardiac operation, erectile dysfunction, hyperaldosteronism, lung fibrosis, scleroderma, anxiety, cognitive disorder, complications caused by immunosuppressor treatment as well as other known diseases associated with the rennin angiotensin aldosterone system.

Functional identification and structure determination of two novel prolidases from cog1228 in the amidohydrolase superfamily

Xiang, Dao Feng,Patskovsky, Yury,Xu, Chengfu,Fedorov, Alexander A.,Fedorov, Elena V.,Sisco, Abby A.,Sauder, J. Michael,Burley, Stephen K.,Almo, Steven C.,Raushel, Frank M.

experimental part, p. 6791 - 6803 (2011/05/05)

Two uncharacterized enzymes from the amidohydrolase superfamily belonging to cog1228 were cloned, expressed, and purified to homogeneity. The two proteins, Sgx9260c (gi|44242006) and Sgx9260b (gi|44479596), were derived from environmental DNA samples originating from the Sargasso Sea. The catalytic function and substrate profiles for Sgx9260c and Sgx9260b were determined using a comprehensive library of dipeptides and N-acyl derivative of l-amino acids. Sgx9260c catalyzes the hydrolysis of Gly-l-Pro, l-Ala-l-Pro, and N-acyl derivatives of l-Pro. The best substrate identified to date is N-acetyl-l-Pro with a value of kcat/Km of 3 × 105 M -1 s-1. Sgx9260b catalyzes the hydrolysis of l-hydrophobic l-Pro dipeptides and N-acyl derivatives of l-Pro. The best substrate identified to date is N-propionyl-l-Pro with a value of kcat/Km of 1 × 105 M-1 s-1. Three-dimensional structures of both proteins were determined by X-ray diffraction methods (PDB codes 3MKV and 3FEQ). These proteins fold as distorted (β/α) 8-barrels with two divalent cations in the active site. The structure of Sgx9260c was also determined as a complex with the N-methylphosphonate derivative of l-Pro (PDB code 3N2C). In this structure the phosphonate moiety bridges the binuclear metal center, and one oxygen atom interacts with His-140. The α-carboxylate of the inhibitor interacts with Tyr-231. The proline side chain occupies a small substrate binding cavity formed by residues contributed from the loop that follows β-strand 7 within the (β/α)8-barrel. A total of 38 other proteins from cog1228 are predicted to have the same substrate profile based on conservation of the substrate binding residues. The structure of an evolutionarily related protein, Cc2672 from Caulobacter crecentus, was determined as a complex with the N-methylphosphonate derivative of l-arginine (PDB code 3MTW).

BACE-1 inhibition by a series of ψ[CH2NH] reduced amide isosteres

Coburn, Craig A.,Stachel, Shawn J.,Jones, Kristen G.,Steele, Thomas G.,Rush, Diane M.,DiMuzio, Jillian,Pietrak, Beth L.,Lai, Ming-Tain,Huang, Qian,Lineberger, Janet,Jin, Lixia,Munshi, Sanjeev,Katharine Holloway,Espeseth, Amy,Simon, Adam,Hazuda, Daria,Graham, Samuel L.,Vacca, Joseph P.

, p. 3635 - 3638 (2007/10/03)

A series of β-site amyloid precursor protein cleaving enzyme (BACE-1) inhibitors containing a ψ(CH2NH) reduced amide bond were synthesized. Incorporation of this reduced amide isostere as a non-cleavable peptide surrogate afforded inhibitors possessing low nanomolar potencies in both an enzymatic and cell-based assay.

Process for the stereoselective preparation of l-alanyl-l-proline

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, (2008/06/13)

L-alanyl-L-proline is stereoselectively prepared catalytically hydrogenating an N-(2-iminopropionyl)-L-proline in the presence of a metal hydrogenolysis catalyst and at a pH of less than about 4. Also disclosed are improved processes for production of N-pyruvyl-L-proline in which L-proline and a 2,2-disubstituted propionyl halide are allowed to react at a pH of at least 9 to produce an L-proline intermediate which is hydrolyzed at a pH range of from about 6.5 to about 8.5 to yield N-pyruvyl-L-proline.

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