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. Author manuscript; available in PMC: 2009 Dec 1.
Published in final edited form as: Bioorg Med Chem. 2008 Oct 11;16(23):10061–10074. doi: 10.1016/j.bmc.2008.10.013

Table 2.

Extended Hippurate Analogs as Substrates

Name Structure
graphic file with name nihms81536t7.jpg 		KM,app (mM) VM,app (s−1) (V/K)app (M−1 s−1) Rel. (V/K)app
3-(2-Furyl)acryloylglycine (26) graphic file with name nihms81536t8.jpg 1.2 ± 0.1 3.4 ± 0.1 (2.8 ± 0.1) × 103 0.45
N-(α-Methylhydrocinnamoyl) glycine (27) R = (C6H5)CH2CH(CH3) 4.1 ± 0.3 18 ± 0.9 (4.3 ± 0.1) × 103 0.69
Acetyl-Gly-Gly (28) R = CH3CONHCH2 1.5 ± 0.070 8.9 ± 0.2 (5.9 ± 0.2) × 103 1.0
Hippuric acid (1) R = C6H5 1.3 ± 0.04 8.2 ± 0.08 (6.2 ± 0.1) × 103 1.0
2-Propylmercaptoacetylglycine(29) R = (CH3)2CHSCH2 0.22 ± 0.01 1.8 ± 0.02 (8.2 ± 0.3) × 103 1.3
N-[(2-Phenylcyclopropyl)carbonyl] glycine (30) graphic file with name nihms81536t9.jpg 0.90 ± 0.07 10 ± 0.3 (1.1 ± 0.07) × 104 1.8
Hydrocinnamoylglycinea (31) R = (C6H5)CH2CH2 0.94 ± 0.1
0.55 ± 0.039 		9.9 ± 0.4 (1.1 ± 0.06) × 104 1.8
N-[(Benzylmercapto)carbonyl] glycine (32) R = (C6H5)CH2S 0.059 ± 0.0070 0.69 ± 0.022 (1.2 ± 0.14) × 104 1.9
CBZ-glycine (33) R = (C6H5)CH2O 0.59 ± 0.02 8.6 ± 0.1 (1.5 ± 0.03) × 104 2.4
Chloroacetyl-Gly-Gly (34) R = ClCH2CONHCH2 0.42 ± 0.03 8.9 ± 0.2 (2.1± 0.1) × 104 3.3
Isocaproylglycine (35) R = (CH3)2CHCH2CH2 0.28 ± 0.03 6.6 ± 0.3 (2.3 ± 0.2) × 104 3.7
tBOC-Gly-Gly (36) R = (CH3)3COCONHCH2 0.30 ± 0.03 7.5 ± 0.2 (2.5 ± 0.1) × 104 4.0
Phenylmercaptoacetylglycin (37) R = (C6H5)SCH2 0.19 ± 0.02 4.6 ± 0.2 (2.5 ± 0.1) × 104 4.0
Phenylhydantoic acida (38) R = (C6H5)NH 0.36 ± 0.08
0.45 ± 0.05 		9.7 ± 0.9 (2.7 ± 0.4) × 104 4.4
Hippuryl-Gly-Gly (39) R = (C6H5)CONHCH2-CONHCH2 0.31 ± 0.06 8.8 ± 1.3 (2.9 ± 0.2) × 104 4.7
Cinnamoylglycine (40) R = (C6H5)CH=CH 0.23 ± 0.02 8.4 ± 0.3 (3.6 ± 0.3) × 104 5.8
3-Phenylthiopropionylglycinea (41) graphic file with name nihms81536t10.jpg 0.038 ± 0.02
0.023 ± 0.002 		1.6 ± 0.2 (4.2 ± 1.4) × 104 6.8
Phenaceturic acid (42) R = (C6H5)CH2 0.16 ± 0.005 7.4 ± 0.09 (4.6 ± 0.09) × 104 7.4
4-Phenylbutyrylglycine (43) R = C6H5(CH2)3 0.16 ± 0.02 11 ± 0.4 (7.0 ± 0.7) × 104 11
4-Nitrobenzoyl-Gly-Gly (44) R = O2NC6H4CONHCH2 0.11 ± 0.007 8.7 ± 0.2 (7.6 ± 0.4) × 104 12
5-Phenylpentanoylglycine (45) R = C6H5(CH2)4 0.15 ± 0.01 12 ± 0.4 (7.6 ± 0.4) × 104 12
8-Phenyloctanoylglycinea (46) R = C6H5(CH2)7 0.10 ± 0.009
0.064 ± 0.006 		8.0 ± 0.3 (7.6 ± 0.4) × 104 12
2-Pyridylmercaptoacetylglycine (47) graphic file with name nihms81536t11.jpg 0.036 ± 0.004 3.0 ± 0.1 (8.3 ± 0.7) × 104 13
Phenylthioacetylglycineb (48) graphic file with name nihms81536t12.jpg 0.024 ± 0.005 2.4 ± 0.2 (1.0 ± 0.2) × 105 16
Hippuryl-Gly (49) R = (C6H5)CONHCH2 0.078 ± 0.011 12 ± 0.8 (1.6 ± 0.1) × 105 26
6-Phenylhexanoylglycinea (50) R = C6H5(CH2)5 0.051 ± 0.007
0.043 ± 0.005 		11 ± 0.4 (2.0 ± 0.2) × 105 32
a

Inhibition of N-dansyl-Tyr-Val-Gly amidation yields the Ki,s value shown in italics.

b

Substrate inhibition observed for this compound, Ki = 3.8 ± 1.3 mM