TABLE 1.

MS and HPLC Characterization of PPADS Analogues Synthesized^a

		FAB (M-H+)		HPLC (rate, min)
Compoundb	Formula	Calculated	Found	System A	System B
2	C14H13O6N3PNa2	396.0337	396.0345	10.15	13.64
4	C14H13O9N3PSNa	451.9929	451.9935	8.84	14.01
8	C15H15O10N3PSNa	482.0035	482.0015	8.80	14.33
9	C15H13O8N3P	394.0440	394.0407	9.14	14.06
10	C15H13O8N3PNa	416.0260	416.0251	7.90	13.94
11	C15H12ON3ClPNa	449.9870	449.9869	8.56	14.18
12	C14H13O6N3ClP	384.0152	384.0155	11.93	14.93
13	C14H12O9N3ClPSNa	485.9540	485.9560	9.40	15.21
14	C15H12O8N3ClPNa	428.0050	428.0049	10.09	15.33
15	C15H12O8N3ClPNa	450.9948	450.9965	7.94	14.07
16	C14H12O8N4ClP	429.0003	428.9997	12.07	15.11
19	C8H10O5NP	230.0218	230.0217	7.63	8.70
20	Cl4Hl1Ol1N3PS2Na3	559.9187	559.9183	8.22	15.22
21	C14H12O8N3ClPSNa	469.9591	469.9583	10.80	14.64
22	C9H12O5NP	244.0375	244.0380	7.54	9.76
23	C15H15O11N3PS2Na3	575.9500	575.9501	8.13	15.62
24	C15H14O8ClPSNa	483.9747	483.9756	10.32	15.00
25	C16H15O7N3P	392.0648	392.0645	8.49	12.41
26	C9H10O5NP	242.0218	242.0220	8.11	9.36
27	C15H12O11N3PS2Na3	571.9187	571.9256	7.13	13.58
28	C10H14O5NP	258.0531	258.0544	8.72	9.39
29	C16H17O11N3PS2Na	543.9862	543.9827	9.19	15.38
30	C16H16O8N3ClPSNa	497.9904	497.9890	11.20	15.18
31	C10H12O5NP	256.0371	256.0375	9.25	10.05
32	C18H14O12N3PS2Na2	581.9654	581.9670	8.37	15.82
33	C18H14O12N3PS2Na2	581.9654	581.9647	8.29	15.78
34	C18H14O15N3PS2Na2	683.9042	683.9044	7.50	16.74

^aMS, mass spectrum; HPLC, high pressure liquid chromatography; PPADS, pyridoxal-6′-phosphate-b-phenylazo-2,4-disulfonate; FAB, fast atom bombardment. System A was 0.1 M triethylammonium acetate buffer:CH₃CN = 95:5 to 40:60 for 20 min wtih flow rate 1 ml/min. System B was 5 mM tetrabutylammonium phosphate buffer:CH₃CN 80:20 to 40:60, in 20 min with flow rate 1 ml/min.

^bStructures are shown in Table 2 and Schemes 1 and 2.