Chemistry–A European Journal

The Interaction of Heteroaryl??Acrylates and Alanines with Phenylalanine Ammonia??Lyase from Parsley

C Paizs, A Katona, J Rétey

Index: Paizs, Csaba; Katona, Adrian; Retey, Janos Chemistry - A European Journal, 2006 , vol. 12, # 10 p. 2739 - 2744

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Citation Number: 29

Abstract

Abstract Acrylic acids and alanines substituted with heteroaryl groups at the β-position were synthesized and spectroscopically characterized (UV, HRMS, 1 H NMR, and 13 C NMR spectroscopy). The heteroaryl groups were furanyl, thiophenyl, benzofuranyl, and benzothiophenyl and contained the alanyl side chains either at the 2-or 3-positions. While the former are good substrates for phenylalanine ammonia-lyase (PAL), the latter ...

 Related Synthetic Route
Thianaphthene Structure

95-15-8

Thianaphthene

~%

Propanedioicacid, 2-(acetylamino)-2-(benzo[b]thien-3-ylmethyl)-, 1,3-diethyl ester Structure

23906-20-9

Propanedioicaci...

(rac)-2-formylamino-3-thiophen-3-yl-propionic acid Structure

811860-66-9

(rac)-2-formyla...

~75%

3-(3-Thienyl)alanine Structure

3685-48-1

3-(3-Thienyl)alanine

3-Thiophenecarboxaldehyde Structure

498-62-4

3-Thiophenecarb...

~%

3-(3-Thienyl)alanine Structure

3685-48-1

3-(3-Thienyl)alanine

3-Chlormethyl-thiophen Structure

2746-23-8

3-Chlormethyl-t...

~%

3-(3-Thienyl)alanine Structure

3685-48-1

3-(3-Thienyl)alanine

3-Thienylmethanol Structure

71637-34-8

3-Thienylmethanol

~%

3-(3-Thienyl)alanine Structure

3685-48-1

3-(3-Thienyl)alanine

2-Furanpropanoic acid, α-(formylamino)- Structure

4066-16-4

2-Furanpropanoi...

~74%

3-(2-Furyl)alanine Structure

4066-39-1

3-(2-Furyl)alanine

4-Ethynylanisole Structure

21535-97-7

4-Ethynylanisole

~%

BENZOFURAN-3-YLMETHANOL Structure

4687-23-4

BENZOFURAN-3-YL...

ethyl 2-(2-acetylphenoxy)acetate Structure

63815-27-0

ethyl 2-(2-acet...

~%

BENZOFURAN-3-YLMETHANOL Structure

4687-23-4

BENZOFURAN-3-YL...

(2-Acetylphenoxy)acetic acid Structure

1878-62-2

(2-Acetylphenox...

~%

BENZOFURAN-3-YLMETHANOL Structure

4687-23-4

BENZOFURAN-3-YL...

Ortho-Hydroxyacetophenone Structure

118-93-4

Ortho-Hydroxyac...

~%

BENZOFURAN-3-YLMETHANOL Structure

4687-23-4

BENZOFURAN-3-YL...

Furfuryl alcohol Structure

98-00-0

Furfuryl alcohol

~%

3-(2-Furyl)alanine Structure

4066-39-1

3-(2-Furyl)alanine

2-formylamino-2-furan-2-yl-methyl-malonic acid diethyl ester Structure

4066-15-3

2-formylamino-2...

~%

3-(2-Furyl)alanine Structure

4066-39-1

3-(2-Furyl)alanine

2-(Chloromethyl)furan Structure

617-88-9

2-(Chloromethyl...

~%

3-(2-Furyl)alanine Structure

4066-39-1

3-(2-Furyl)alanine

N/A Structure

127682-11-5

N/A

~%

3-(2-Furyl)alanine Structure

4066-39-1

3-(2-Furyl)alanine

3-(chloromethyl)-1-benzothiophene Structure

3216-47-5

3-(chloromethyl...

~30%

1-Benzothiophene-3-carbaldehyde Structure

5381-20-4

1-Benzothiophen...

3-(chloromethyl)-1-benzothiophene Structure

3216-47-5

3-(chloromethyl...

~%

3-(1-Benzothiophen-3-yl)-L-alanine Structure

1956-23-6

3-(1-Benzothiop...

Propanedioicacid, 2-(acetylamino)-2-(benzo[b]thien-3-ylmethyl)-, 1,3-diethyl ester Structure

23906-20-9

Propanedioicaci...

~%

3-(1-Benzothiophen-3-yl)-L-alanine Structure

1956-23-6

3-(1-Benzothiop...

3-(2-thienyl)acrylic acid ethyl ester Structure

13979-15-2

3-(2-thienyl)ac...

~89%

3-(2-Thienyl)Acrylic Acid Structure

1124-65-8

3-(2-Thienyl)Ac...

3-(2-Furyl)alanine Structure

4066-39-1

3-(2-Furyl)alanine

~44%

D-2-Furylalanine Structure

110772-46-8

D-2-Furylalanine

Furylacrylic acid Structure

539-47-9

Furylacrylic acid

~67%

3-(2-Furyl)alanine Structure

121786-31-0

3-(2-Furyl)alanine

Thianaphthene Structure

95-15-8

Thianaphthene

~%

3-(1-Benzothiophen-3-yl)-L-alanine Structure

1956-23-6

3-(1-Benzothiop...

3-Furanpropanoic acid, α-(formylamino)- Structure

128941-47-9

3-Furanpropanoi...

~76%

2-amino-3-(furan-3-yl)propanoic acid Structure

3685-52-7

2-amino-3-(fura...

3-Furaldehyde Structure

498-60-2

3-Furaldehyde

~%

2-amino-3-(furan-3-yl)propanoic acid Structure

3685-52-7

2-amino-3-(fura...

3-(Chloromethyl)furan Structure

14497-29-1

3-(Chloromethyl...

~%

2-amino-3-(furan-3-yl)propanoic acid Structure

3685-52-7

2-amino-3-(fura...

3-Furancarbinol Structure

4412-91-3

3-Furancarbinol

~%

2-amino-3-(furan-3-yl)propanoic acid Structure

3685-52-7

2-amino-3-(fura...

2-formylamino-2-furan-3-yl-methyl-malonic acid diethyl ester Structure

128941-43-5

2-formylamino-2...

~%

2-amino-3-(furan-3-yl)propanoic acid Structure

3685-52-7

2-amino-3-(fura...

N/A Structure

128941-45-7

N/A

~%

2-amino-3-(furan-3-yl)propanoic acid Structure

3685-52-7

2-amino-3-(fura...

2-acetylamino-2-benzofuran-3-yl-methyl-malonic acid diethyl ester Structure

1023290-69-8

2-acetylamino-2...

~%

2-AMINO-3-(BENZOFURAN-3-YL)PROPANOIC ACID Structure

72071-49-9

2-AMINO-3-(BENZ...

4-Ethynylanisole Structure

21535-97-7

4-Ethynylanisole

~%

2-AMINO-3-(BENZOFURAN-3-YL)PROPANOIC ACID Structure

72071-49-9

2-AMINO-3-(BENZ...

BENZOFURAN-3-YLMETHANOL Structure

4687-23-4

BENZOFURAN-3-YL...

~%

2-AMINO-3-(BENZOFURAN-3-YL)PROPANOIC ACID Structure

72071-49-9

2-AMINO-3-(BENZ...

Benzofuran-3-carbaldehyde Structure

4687-25-6

Benzofuran-3-ca...

~%

2-AMINO-3-(BENZOFURAN-3-YL)PROPANOIC ACID Structure

72071-49-9

2-AMINO-3-(BENZ...

3-(chloromethyl)-1-benzofuran Structure

67713-99-9

3-(chloromethyl...

~%

2-AMINO-3-(BENZOFURAN-3-YL)PROPANOIC ACID Structure

72071-49-9

2-AMINO-3-(BENZ...

ethyl 2-(2-acetylphenoxy)acetate Structure

63815-27-0

ethyl 2-(2-acet...

~%

2-AMINO-3-(BENZOFURAN-3-YL)PROPANOIC ACID Structure

72071-49-9

2-AMINO-3-(BENZ...

(2-Acetylphenoxy)acetic acid Structure

1878-62-2

(2-Acetylphenox...

~%

2-AMINO-3-(BENZOFURAN-3-YL)PROPANOIC ACID Structure

72071-49-9

2-AMINO-3-(BENZ...

Ortho-Hydroxyacetophenone Structure

118-93-4

Ortho-Hydroxyac...

~%

2-AMINO-3-(BENZOFURAN-3-YL)PROPANOIC ACID Structure

72071-49-9

2-AMINO-3-(BENZ...

BENZOFURAN-3-YLMETHANOL Structure

4687-23-4

BENZOFURAN-3-YL...

~%

3-(chloromethyl)-1-benzofuran Structure

67713-99-9

3-(chloromethyl...

4-Ethynylanisole Structure

21535-97-7

4-Ethynylanisole

~%

3-(chloromethyl)-1-benzofuran Structure

67713-99-9

3-(chloromethyl...

Benzofuran-3-carbaldehyde Structure

4687-25-6

Benzofuran-3-ca...

~%

3-(chloromethyl)-1-benzofuran Structure

67713-99-9

3-(chloromethyl...

ethyl 2-(2-acetylphenoxy)acetate Structure

63815-27-0

ethyl 2-(2-acet...

~%

3-(chloromethyl)-1-benzofuran Structure

67713-99-9

3-(chloromethyl...

(2-Acetylphenoxy)acetic acid Structure

1878-62-2

(2-Acetylphenox...

~%

3-(chloromethyl)-1-benzofuran Structure

67713-99-9

3-(chloromethyl...

Ortho-Hydroxyacetophenone Structure

118-93-4

Ortho-Hydroxyac...

~%

3-(chloromethyl)-1-benzofuran Structure

67713-99-9

3-(chloromethyl...

3-Thiophenecarboxaldehyde Structure

498-62-4

3-Thiophenecarb...

~%

3-Chlormethyl-thiophen Structure

2746-23-8

3-Chlormethyl-t...

ethyl 2-(2-acetylphenoxy)acetate Structure

63815-27-0

ethyl 2-(2-acet...

~%

Benzofuran-3-carbaldehyde Structure

4687-25-6

Benzofuran-3-ca...

(2-Acetylphenoxy)acetic acid Structure

1878-62-2

(2-Acetylphenox...

~%

Benzofuran-3-carbaldehyde Structure

4687-25-6

Benzofuran-3-ca...

Ortho-Hydroxyacetophenone Structure

118-93-4

Ortho-Hydroxyac...

~%

Benzofuran-3-carbaldehyde Structure

4687-25-6

Benzofuran-3-ca...

Coumarone Structure

271-89-6

Coumarone

~%

2-chloromethylbenzofuran Structure

36754-60-6

2-chloromethylb...

Benzo[b]furan-2-carboxaldehyde Structure

4265-16-1

Benzo[b]furan-2...

~%

2-chloromethylbenzofuran Structure

36754-60-6

2-chloromethylb...

Thianaphthene Structure

95-15-8

Thianaphthene

~%

ethyl 3-(1-benzothiophen-2-yl)prop-2-enoate Structure

133280-03-2

ethyl 3-(1-benz...

H-3-DL-Ala(2-thienyl)-OH Structure

2021-58-1

H-3-DL-Ala(2-th...

~45%

3-(2-Thienyl)-L-alanine Structure

62561-76-6

3-(2-Thienyl)-L...

1-Benzothiophene-3-carbaldehyde Structure

5381-20-4

1-Benzothiophen...

~%

(2E)-2-(HYDROXYIMINO)-N-(3-NITROPHENYL)ACETAMIDE Structure

5381-29-3

(2E)-2-(HYDROXY...

3-(chloromethyl)-1-benzothiophene Structure

3216-47-5

3-(chloromethyl...

~%

(2E)-2-(HYDROXYIMINO)-N-(3-NITROPHENYL)ACETAMIDE Structure

5381-29-3

(2E)-2-(HYDROXY...

Thianaphthene Structure

95-15-8

Thianaphthene

~%

(2E)-2-(HYDROXYIMINO)-N-(3-NITROPHENYL)ACETAMIDE Structure

5381-29-3

(2E)-2-(HYDROXY...

3-(1-Benzothiophen-3-yl)-L-alanine Structure

72120-71-9

3-(1-Benzothiop...

~%

(2E)-2-(HYDROXYIMINO)-N-(3-NITROPHENYL)ACETAMIDE Structure

5381-29-3

(2E)-2-(HYDROXY...

3-(1-Benzothiophen-3-yl)-L-alanine Structure

1956-23-6

3-(1-Benzothiop...

~%

(2E)-2-(HYDROXYIMINO)-N-(3-NITROPHENYL)ACETAMIDE Structure

5381-29-3

(2E)-2-(HYDROXY...

3-(1-Benzothiophen-3-yl)-L-alanine Structure

111139-55-0

3-(1-Benzothiop...

(E)-3-benzofuran-2-yl-acrylic acid ethyl ester Structure

125482-23-7

(E)-3-benzofura...

~94%

(2E)-3-(1-Benzofuran-2-Yl)Acrylic Acid Structure

132376-67-1

(2E)-3-(1-Benzo...

Benzo[b]furan-2-carboxaldehyde Structure

4265-16-1

Benzo[b]furan-2...

~%

(2E)-3-(1-Benzofuran-2-Yl)Acrylic Acid Structure

132376-67-1

(2E)-3-(1-Benzo...

2-Propenoic acid,3-(2-furanyl)-, ethyl ester Structure

623-20-1

2-Propenoic aci...

~92%

Furylacrylic acid Structure

539-47-9

Furylacrylic acid


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