Protein Backbone Modification by Novel C. alpha.-C Side-Chain Scission

D Ranganathan, NK Vaish, K Shah

Index: Ranganathan; Vaish; Shah Journal of the American Chemical Society, 1994 , vol. 116, # 15 p. 6545 - 6557

Full Text: HTML

Citation Number: 66

Abstract

Abstract: a-Ketoamide (-NH-CO-CO-) units in intact peptides are generated from Ser/Thr residues via Ru (VII1)-catalyzed C=-C side-chain scission. Facets associated with this novel a-carbon modification have been probed with 75 peptides chosen to represent every possible peptide environment. The reactions were carried out at room temperature with in situ generated Ru (VII1) in biphasic (CH3CN/CC4/pH 3 phosphate buffer, 1: 1: 2 v/v) ...

 Related Synthetic Route
N-Cbz-L-serine methyl ester Structure

1676-81-9

N-Cbz-L-serine ...

~81%

Z-Ser-NH2 Structure

70897-15-3

Z-Ser-NH2

diazomethane Structure

186581-53-3

diazomethane

n-benzoyl-l-threonine Structure

27696-01-1

n-benzoyl-l-thr...

~79%

bz-thr-ome Structure

79893-89-3

bz-thr-ome

Z-Leu-OH Structure

2018-66-8

Z-Leu-OH

~50%

z-val-nh2 Structure

13139-28-1

z-val-nh2

Z-Leu-Ser-Ser-Leu-Leu-Ser-Leu-OMe Structure

158011-13-3

Z-Leu-Ser-Ser-L...

~11%

(S)-BENZYL (1-AMINO-4-METHYL-1-OXOPENTAN-2-YL)CARBAMATE Structure

4801-79-0

(S)-BENZYL (1-A...

N/A Structure

158011-07-5

N/A

~%

(S)-BENZYL (1-AMINO-4-METHYL-1-OXOPENTAN-2-YL)CARBAMATE Structure

4801-79-0

(S)-BENZYL (1-A...

Cyclo(-Ser-Ser) Structure

23409-30-5

Cyclo(-Ser-Ser)

~30%

2,3,5,6-Piperazinetetrone Structure

49715-78-8

2,3,5,6-Piperaz...

Bz-Gly-Thr-OMe Structure

115494-73-0

Bz-Gly-Thr-OMe

~72%

Hippuramide Structure

5813-81-0

Hippuramide

N-Cbz-L-Serine Structure

1145-80-8

N-Cbz-L-Serine

H-Ser-Ome·HCl Structure

5680-80-8

H-Ser-Ome·HCl

~60%

methyl 3-hydroxy-2-[(3-hydroxy-2-phenylmethoxycarbonylamino-propanoyl)amino]propanoate Structure

5874-76-0

methyl 3-hydrox...

N/A Structure

131458-24-7

N/A

~81%

Bz-L-Phe-NH2 Structure

72150-35-7

Bz-L-Phe-NH2

Bz-Phe-Thr-OMe Structure

131458-30-5

Bz-Phe-Thr-OMe

~66%

Bz-L-Phe-NH2 Structure

72150-35-7

Bz-L-Phe-NH2

N-Benzoyl-L-phenylalanine Structure

2566-22-5

N-Benzoyl-L-phe...

~%

Bz-L-Phe-NH2 Structure

72150-35-7

Bz-L-Phe-NH2

bz-thr-ome Structure

79893-89-3

bz-thr-ome

~82%

Benzamide Structure

55-21-0

Benzamide

Bz-L-Ser-OMe Structure

10144-46-4

Bz-L-Ser-OMe

~74%

Benzamide Structure

55-21-0

Benzamide

methyl Z-glycyl-L-serinate Structure

108849-83-8

methyl Z-glycyl...

~92%

z-gly-nh2 Structure

949-90-6

z-gly-nh2

Cbz-Gly-L-Thr-OMe Structure

41961-03-9

Cbz-Gly-L-Thr-OMe

~92%

z-gly-nh2 Structure

949-90-6

z-gly-nh2

methyl 2-[(3-hydroxy-2-phenylmethoxycarbonylamino-propanoyl)amino]-4-methyl-pentanoate Structure

17331-94-1

methyl 2-[(3-hy...

~90%

N-Benzyloxycarbonylserylleucinamide Structure

17331-87-2

N-Benzyloxycarb...

methyl L-leucinate Structure

2666-93-5

methyl L-leucinate

~%

N-Benzyloxycarbonylserylleucinamide Structure

17331-87-2

N-Benzyloxycarb...


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