. Author manuscript; available in PMC: 2017 Mar 1.

Published in final edited form as: Bioorg Med Chem. 2016 Jan 6;24(5):938–956. doi: 10.1016/j.bmc.2016.01.007

Table 3.

Activity of LAP toward amino acid prodrug conjugates

Compound	Prodrug Type	% Cleavage^a	Specific Activity of LAP (μM/min/enzyme unit)
15	Serinamide	62%	1.2
16	Glycinamide	100%	180
17	Serinamide	90%	C^e
18	Glycinamide	100%	C^e
22	Serinamide	NC	ND
23	Serinamide	NC	ND
24	Glycinamide	C^b	ND
38	Serinamide	C^c, <10%	ND
39	Serinamide	C^c, <10%	ND
44	Glycinamide	100%	15.5
45	Glycinamide	100%	0.12
3' CA4-L- serinamide	Serinamide	C^d, 95%	ND
AVE8062	Serinamide	C^d, 95%	ND

Percentage of cleavage is calculated based on the area ratio of the parent drug and prodrug at a specific wavelength. NC: No cleavage observed using 1.5 units LAP. C: Cleaved (a rate study was not carried out).

, disappearance of the bis-glycinamide prodrug 24 was observed, but less than 50% of the expected final product 8 was detected.

, the serinamide prodrug was cleaved, but less than 10% of the expected product was obtained.

, used as positive controls.⁵²

, the prodrug was readily cleaved, but the absolute rate could not be determined because the parent compound (E-isomer of 2' CA4-amine) was not available since isomerization (Z to E took place as a byproduct during salt formation after installation of the amino acid prodrug).

ND: Not determined