Tetrahedron letters

Remarkable effects of donor esters on the α-chymotrypsin-catalyzed couplings of inherently poor amino acid substrates

T Miyazawa, K Tanaka, E Ensatsu, R Yanagihara…

Index: Miyazawa, Toshifumi; Tanaka, Kayoko; Ensatsu, Eiichi; Yanagihara, Ryoji; Yamada, Takashi Tetrahedron Letters, 1998 , vol. 39, # 9 p. 997 - 1000

Full Text: HTML

Citation Number: 17

Abstract

The extremely low efficiency during the α-chymotrypsin-catalyzed coupling of an inherently poor amino acid substrate, eg, alanine, using the methyl ester as an acyl donor was significantly improved using esters such as the 2, 2, 2-trifluoroethyl or carbamoylmethyl ester. The ameliorating effect of the latter ester was especially significant.

 Related Synthetic Route
Z-L-Ala-OCam Structure

4816-87-9

Z-L-Ala-OCam

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

~0%

N-Carbobenzyloxy-L-alanine Structure

1142-20-7

N-Carbobenzylox...

Z-Ala-Leu-NH2 Structure

18323-56-3

Z-Ala-Leu-NH2

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

Cbz-L-Ala-OTfe Structure

203640-41-9

Cbz-L-Ala-OTfe

~0%

N-Carbobenzyloxy-L-alanine Structure

1142-20-7

N-Carbobenzylox...

Z-Ala-Leu-NH2 Structure

18323-56-3

Z-Ala-Leu-NH2

N/A Structure

4821-81-2

N/A

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

~0%

N-Carbobenzyloxy-L-alanine Structure

1142-20-7

N-Carbobenzylox...

Z-Ala-Leu-NH2 Structure

18323-56-3

Z-Ala-Leu-NH2

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

N/A Structure

203640-48-6

N/A

~0%

N-Carbobenzyloxy-L-alanine Structure

1142-20-7

N-Carbobenzylox...

Z-Ala-Leu-NH2 Structure

18323-56-3

Z-Ala-Leu-NH2

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

N/A Structure

203640-42-0

N/A

~0%

N-Carbobenzyloxy-L-alanine Structure

1142-20-7

N-Carbobenzylox...

Z-Ala-Leu-NH2 Structure

18323-56-3

Z-Ala-Leu-NH2

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

Z-L-Ala methoxymethyl ester Structure

203640-47-5

Z-L-Ala methoxy...

~0%

N-Carbobenzyloxy-L-alanine Structure

1142-20-7

N-Carbobenzylox...

Z-Ala-Leu-NH2 Structure

18323-56-3

Z-Ala-Leu-NH2

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

Z-L-Ala acetonyl ester Structure

65479-15-4

Z-L-Ala acetony...

~0%

N-Carbobenzyloxy-L-alanine Structure

1142-20-7

N-Carbobenzylox...

Z-Ala-Leu-NH2 Structure

18323-56-3

Z-Ala-Leu-NH2

Z-L-Ala 2-chloroethyl ester Structure

130446-89-8

Z-L-Ala 2-chlor...

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

~0%

N-Carbobenzyloxy-L-alanine Structure

1142-20-7

N-Carbobenzylox...

Z-Ala-Leu-NH2 Structure

18323-56-3

Z-Ala-Leu-NH2

Z-Gly carbamoylmethyl ester Structure

4816-85-7

Z-Gly carbamoyl...

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

~92%

Z-Gly-Leu-NH2 Structure

7535-72-0

Z-Gly-Leu-NH2

Z-Gly-OH Structure

1138-80-3

Z-Gly-OH

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

N/A Structure

203640-50-0

N/A

~74%

Z-Gly-Leu-NH2 Structure

7535-72-0

Z-Gly-Leu-NH2

Z-Gly-OH Structure

1138-80-3

Z-Gly-OH

Z-L-Ala 2,2,2-trichloroethyl ester Structure

67850-37-7

Z-L-Ala 2,2,2-t...

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

~0%

N-Carbobenzyloxy-L-alanine Structure

1142-20-7

N-Carbobenzylox...

Z-Ala-Leu-NH2 Structure

18323-56-3

Z-Ala-Leu-NH2

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

Z-L-Ser-OCam Structure

194658-69-0

Z-L-Ser-OCam

~94%

N-Cbz-L-Serine Structure

1145-80-8

N-Cbz-L-Serine

N-Benzyloxycarbonylserylleucinamide Structure

17331-87-2

N-Benzyloxycarb...

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

N/A Structure

203640-51-1

N/A

~87%

N-Cbz-L-Serine Structure

1145-80-8

N-Cbz-L-Serine

N-Benzyloxycarbonylserylleucinamide Structure

17331-87-2

N-Benzyloxycarb...

N-Cbz-L-serine methyl ester Structure

1676-81-9

N-Cbz-L-serine ...

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

~9%

N-Cbz-L-Serine Structure

1145-80-8

N-Cbz-L-Serine

N-Benzyloxycarbonylserylleucinamide Structure

17331-87-2

N-Benzyloxycarb...

H-Leu-NH2.HCl Structure

10466-61-2

H-Leu-NH2.HCl

N/A Structure

203640-57-7

N/A

~7%

Z-D-Ala-OH Structure

26607-51-2

Z-D-Ala-OH

Z-Ala-Leu-NH2 Structure

18323-56-3

Z-Ala-Leu-NH2


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