. 2013 Aug 22;61(38):9015–9026. doi: 10.1021/jf401960m

Table 1. Peak Numbers, Retention Times, and Peak Assignments for All Compounds Detected in the Silylated Ammoxidation Products of d-Glucose and d-Xylose.

compound number	retention time (min)	compound name
Sugars
58	31.08, 31.24, 31.33, 32.66	fructose, pentakis(TMS)
63	32.84, 34.67	glucose, pentakis(TMS)
64	32.94	mannose, pentakis(TMS)
88	30.06	xylose, tetrakis(TMS)
Amino Sugars
62	32.36	glucosamine, tetrakis(TMS)^a
62	33.29	glucosamine, hexakis(TMS)
65	33.74	fructosamine, hexakis(TMS)^b
69	37.98, 38.17, 38.58, 39.31	aminohexopyranosid, hexakis(TMS)^b
71	41.15, 41.47, 41.76, 41.88, 42.01, 42.50, 46.26, 46.69, 47.10, 48.39, 49.57, 49.76, 49.94	aminoglycosides of unknown constitution^b
73	47.56	di(glucopyranosyl)amine, octakis(TMS)^b
Carboxylic Acids
35	11.87	lactic acid, bis(TMS)^a
36	12.30	glycolic acid, bis(TMS)^a
37	14.01	oxalic acid, bis(TMS) ester^a
38	14.28	3-hydroxypropanoic acid, bis(TMS)^a
42	19.66	glyceric acid, tris(TMS)^d
45	21.78	2,4-dihydroxybutyric acid, tris(TMS)^a
46	22.34	3,4-dihydroxybutyric acid, tris(TMS)^a
49	25.21	erythronic acid, tetrakis(TMS)^a
50	25.62	threonic acid, tetrakis(TMS)^a
53	27.79	2-deoxypentonic acid, tetrakis(TMS)^d
54	27.96	3-deoxypentonic acid, tetrakis(TMS)^d
56	30.26	ribonic acid, pentakis(TMS)^a
57	30.61	arabinoic acid, pentakis(TMS)^a
89	30.44	xylonic acid, pentakis(TMS)^a
60	32.14	2-deoxyhexonic acid, pentakis(TMS)^b
61	32.25	3-deoxyhexonic acid, pentakis(TMS)^d
66	34.37, 35.06	hexonic acid, hexakis(TMS)^d
Carboxylic Acid Amides
86	7.16	acetic amide^a
6	15.03	lactamide, bis(TMS)^a
7	15.63	glycolamide, bis(TMS)^a (coeluting with pyrazinylmethanol)
10	17.25	urea, N,N′-bis(TMS)^a
32	8.61, 11.00	bis(TMS) formamide (two peaks)^a
33	8.95	carbodiimide, N,N′-bis(TMS) (from urea)^a
34	11.00, 15.95	carbamate, bis(TMS) and -tris(TMS)^a
39	17.51	oxamic acid, bis(TMS)^b
Amino Carboxylic Acids
41	13.56, 18.83	glycine, bis(TMS) and -tris(TMS)^a
47	23.20	2-aminomalonic acid, tris(TMS)^d
74	13.07	alanine, bis(TMS)^a
75	17.50, 20.43	serine, bisTMS and −trisTMS^a
52	21.59	β-alanine, tris(TMS)^d
1H-Imidazoles
2	12.87	1H-imidazole (TMS)^a
5	14.68	4-methyl-1H-imidazole (TMS)^a
43	20.90	4-hydroxymethyl-1H-imidazole, bis(TMS)^a
55	28.79	4-(1,2-dihydroxyethyl)-1H-imidazole, tris(TMS)^b
68	35.92	4-(d-arabino-tetrahydroxybutyl)-1H-imidazole, pentakis(TMS)^a
77	36.22	2-acetyl-4-(tetrahydroxybutyl)-1H-imidazole, pentakis(TMS^b
90	31.87	4(5)-(trihydroxypropyl)-1H-imidazole, tris-O-(TMS)^b
Pyridines
4	13.90	3-hydroxypyridine, TMS^a
20	24.60	2-(hydroxymethyl)-pyridin-5-ol, bis(TMS)^b
Pyrazines
1	11.85	2-pyrazinol, TMS^a
3	13.02	2-hydroxy-5-methylpyrazine, TMS or isomer^b
7	15.61	2-pyrazinylmethanol, TMS^a
8	15.83	2-hydroxy-3-methylpyrazine, TMS or isomer^b
12	17.94	2-hydroxymethyl-6-methylpyrazine, TMS^a
18	23.45	2-(dihydroxyethyl)pyrazine, bis(TMS)^c
21	24.77, 25.10, 25.36, 25.83, xylose only: 24.23	2-(dihydroxyethyl)-5-methyl-pyrazine, bis(TMS)^b and isomers
22	26.34, 26.57	2,5^a- and 2,6^b-bis(hydroxymethyl)pyrazine, bis(TMS)
23	31.76	2-(dihydroxyethyl)-5(hydroxymethyl)pyrazine, tris(TMS)^b
24	33.07	2-(tetrahydroxybutyl)pyrazine, tetrakis(TMS)^b
25	33.45, 33.60, 33.75, 33.90	2-(tetrahydroxybutyl)-5-methyl-pyrazine, tetrakis(TMS)^b and isomers
28	28.76, 28.91	2-(trihydroxypropyl)pyrazine, tris(TMS)^b, 2 isomers
29	29.48, 29.58, 29.76, 29.86	2-(trihydroxybutyl)-5-methylpyrazine, tris(TMS) and isomers^b
30	34.90, 35.50	2-(trihydroxybutyl)-5-(hydroxymethyl)pyrazine, tetrakis(TMS) and isomers^b
78	36.10, 36.34	2-hydroxy-5 (and 6)-(tetrahydroxybutyl)pyrazine, pentakis(TMS)^b
79	37.96, 38.36	2-(hydroxymethyl)-5 (and 6)-(tetrahydroxybutyl)pyrazine, pentakis(TMS)^b
80	39.24, 39.79	2-(2-hydroxyethyl)-5 (and 6)-tetrahydroxybutyl pyrazine, pentakis(TMS)^b
81	41.23, 41.58	2-(dihydroxyethyl)-5 (and 6)-tetrahydroxybutyl pyrazine, hexakis(TMS)^b
82	42.92, 43.37	2-(2,3-dihydroxypropyl)-5 (and 6)-tetrahydroxybutyl pyrazine, hexakis(TMS)^b
83	43.92, 44.40	2-(trihydroxypropyl)-5 (and 6)-tetrahydroxybutyl pyrazine, hexakis(TMS)^b
84	46.03, 46.08	2,5- and 2,6-deoxyfructosazine, heptakis(TMS)^b
85	46.87, 7.11, 48.07,48.28	2,5- and 2,6-fructosazine and diastereomers, octakis(TMS)^b
87	29.51, 29.81	2-methyl-5 (and 6)-(trihydroxypropyl)pyrazine, tetrakis(TMS)^b
93	34.77, 34.83, 35.23, 35.44	2-hydroxymethyl-5(and 6)-(trihydroxypropyl) pyrazine, tetrakis (TMS)^b
94	35.96, 36.08, 36.54, 36.79, 36.95, 37.80	2-(hydroxyethyl)-5-(trihydroxypropyl)pyrazine, tetrakis(TMS) and isomers^b
95	38.15, 39.01	2-dihydroxyethyl-5 (and 6)-trihydroxybutyl pyrazine, pentakis TMS^b
96	39.88, 40.89	2-(dihydroxypropyl)-5 (and 6)-trihydroxypropyl pyrazine, hexakis(TMS)^b
97	40.94, 41.10, 41.55, 41.91	2,5- and 2,6-trihydroxypropyl pyrazine, hexakis(TMS)^b
Others and Unknown
11	17.75	DMAP (catalyst)^a
13	18.66	2-methylquinoxaline (added)^a
31	8.44	trifluoromethyl-bis-(trimethylsilyl)methyl ketone (silylation artifact)^d
40	18.09	phosphate, tris(TMS) ester (internal standard)^a
51	27.05	M⁺ = 272
59	32.00	M⁺ = 525
70	40.50	phenyl-α-glucopyranosid (internal standard)^a
9	16.69	M⁺ = 196
14	19.40, 19.52	M⁺ = 180
15	20.08–20.70	mixture of low abundance compounds
16	22.27	M⁺ = 321
17	23.01	M⁺ = 270
19	23.84	M⁺ = 331
26, 27	21.18, 22.03	M⁺ = 256
44	21.09	M⁺ = 249
45	21.59	M⁺ = 244
48	21.99	M⁺ = 248
51	23.22	M⁺ = 242
67	27.05	M⁺ = 272
72	34.49	M⁺ = 493
76	45.88	M⁺ = 502
91	35.13	M⁺ = 459
92	33.21, 33.70	M⁺ = 400
98	31.59, 31.70	M⁺ = 414

Identified by comparison with authentic samples.

Tentative assignment from fragmentation patterns.

Assignment from comparison with literature data.³³⁻³⁵

Assignment according to NIST 2008 database.