J Food Bioact

Journal of Food Bioactives, ISSN 2637-8752 print, 2637-8779 online

Journal website www.isnff-jfb.com

Original Research

Volume 20, December 2022, pages 90-97

Reactivity comparison of Amadori rearrangement product formation of glycine, diglycine, and triglycine in a competing Maillard system

Figure 1. LC/MS/MS analysis of glycine-ARP: full scan spectrum (a); secondary spectrum (b); proposed fragmentation pathway (c). (120.0 v–m/z: 76.1, 118.0, 156.1, 174.0, 202.0, 220.0, 238.0)

Figure 2. LC/MS/MS analysis of diglycine-ARP: full scan spectrum (a); secondary spectrum (b); proposed fragmentation pathway (c). (90.0 v–m/z: 76.2, 133.0, 211.0, 240.9, 259.1, 277.1, 295.1)

Figure 3. LC/MS/MS analysis of triglycine-ARP: full scan spectrum (a); secondary spectrum (b); proposed fragmentation pathway (c). 90.0v–m/z: 190.1, 211.1, 268.1, 298.1, 316.1, 334.1, 352.

Figure 4. Browning intensity change under different initial pH and temperature in relative reactivity analysis. *1h and 2h means thermal treatment of 1 hour and 2 hours, receptivity. *R1 and R2 means the model system of glucose/glycine/diglycine = 1:1:1 and glucose/glycine/triglycine = 1:1:1 (molar ratio), respectively.

**Table 1.** Actual contents of glycine-ARP and diglycine-ARP formed in combination reaction mode (R1, mmol/L)
	GA (R1)	DA (R1)
1H and 2H means thermal treatment of 1 hour and 2 hours, receptivity. R1 means the model system of glucose/glycine/diglycine = 1:1:1 (molar ratio).
80 °C 1H	0.0021	0.0033	0.0035	0.0695	0.0025	0.0035	0.0068	0.0059
80 °C 2H	0.0021	0.0043	0.0058	0.1099	0.0021	0.0043	0.0081	0.0092
100 °C 1H	0.0049	0.0061	0.0063	0.1905	0.0047	0.0088	0.0146	0.0143
100 °C 2H	0.0080	0.0172+	0.0218	0.3049	0.0077	0.0159	0.0282	0.0254
130 °C 1H	0.0563	0.2000	0.3825	0.2724	0.0465	0.1029	0.1235	0.1469
130 °C 2H	0.0637	0.3514	0.3238	0.2520	0.0479	0.0981	0.1121	0.1440
160 °C 1H	0.0543	0.1832	0.0793	0.0260	0.0523	0.0690	0.0739	0.0462
160 °C 2H	0.0326	0.2963	0.2223	0.0421	0.0315	0.0397	0.0439	0.0136

Table 1. Actual contents of glycine-ARP and diglycine-ARP formed in combination reaction mode (R1, mmol/L)

GA (R1)

DA (R1)

pH 3

pH 5

pH 7

pH 9

pH 3

pH 5

pH 7

pH 9

*1H and 2H means thermal treatment of 1 hour and 2 hours, receptivity. *R1 means the model system of glucose/glycine/diglycine = 1:1:1 (molar ratio).

80 °C 1H

0.0021

0.0033

0.0035

0.0695

0.0025

0.0035

0.0068

0.0059

80 °C 2H

0.0021

0.0043

0.0058

0.1099

0.0021

0.0043

0.0081

0.0092

100 °C 1H

0.0049

0.0061

0.0063

0.1905

0.0047

0.0088

0.0146

0.0143

100 °C 2H

0.0080

0.0172+

0.0218

0.3049

0.0077

0.0159

0.0282

0.0254

130 °C 1H

0.0563

0.2000

0.3825

0.2724

0.0465

0.1029

0.1235

0.1469

130 °C 2H

0.0637

0.3514

0.3238

0.2520

0.0479

0.0981

0.1121

0.1440

160 °C 1H

0.0543

0.1832

0.0793

0.0260

0.0523

0.0690

0.0739

0.0462

160 °C 2H

0.0326

0.2963

0.2223

0.0421

0.0315

0.0397

0.0439

0.0136

**Table 2.** Actual contents of glycine-ARP and triglycine-ARP formed in combination reaction mode (R2, mmol/L)
	GA (R2)	TA (R2)	DA (R2, from TA degradation)
1H and 2H means thermal treatment of 1 hour and 2 hours, receptivity. R2 means the model system of glucose/glycine/triglycine = 1:1:1 (molar ratio).
80 °C 1H	0.0053	0.0128	0.0105	0.0876	0.0042	0.0123	0.0101	0.0129
80 °C 2H	0.0042	0.0065	0.0091	0.1166	0.0055	0.0065	0.0080	0.0198
100 °C 1H	0.0065	0.0161	0.0251	0.1604	0.0053	0.0129	0.0107	0.0213
100 °C 2H	0.0085	0.0211	0.0262	0.2502	0.0074	0.0189	0.0139	0.0222
130 °C 1H	0.0854	0.1662	0.1773	0.1319	0.0758	0.0988	0.1711	0.1299	0.0027	0.0029	0.0031	0.0073
130 °C 2H	0.1205	0.1231	0.1164	0.0788	0.0623	0.0996	0.1108	0.0896	0.0026	0.0025	0.0034	0.0069
160 °C 1H	0.0326	0.2506	0.0642	0.0520	0.0132	0.0111	0.0107	0.0209	0.0034	0.0048	0.0029	0.0056
160 °C 2H	0.0156	0.0593	0.0568	0.0487	0.0143	0.0018	0.0010	0.0024	0.0048	0.0030	0.0031	0.0035

Table 2. Actual contents of glycine-ARP and triglycine-ARP formed in combination reaction mode (R2, mmol/L)

GA (R2)

TA (R2)

DA (R2, from TA degradation)

pH 3

pH 5

pH 7

pH 9

pH 3

pH 5

pH 7

pH 9

pH 3

pH 5

pH 7

pH 9

*1H and 2H means thermal treatment of 1 hour and 2 hours, receptivity. *R2 means the model system of glucose/glycine/triglycine = 1:1:1 (molar ratio).

80 °C 1H

0.0053

0.0128

0.0105

0.0876

0.0042

0.0123

0.0101

0.0129

80 °C 2H

0.0042

0.0065

0.0091

0.1166

0.0055

0.0065

0.0080

0.0198

100 °C 1H

0.0065

0.0161

0.0251

0.1604

0.0053

0.0129

0.0107

0.0213

100 °C 2H

0.0085

0.0211

0.0262

0.2502

0.0074

0.0189

0.0139

0.0222

130 °C 1H

0.0854

0.1662

0.1773

0.1319

0.0758

0.0988

0.1711

0.1299

0.0027

0.0029

0.0031

0.0073

130 °C 2H

0.1205

0.1231

0.1164

0.0788

0.0623

0.0996

0.1108

0.0896

0.0026

0.0025

0.0034

0.0069

160 °C 1H

0.0326

0.2506

0.0642

0.0520

0.0132

0.0111

0.0107

0.0209

0.0034

0.0048

0.0029

0.0056

160 °C 2H

0.0156

0.0593

0.0568

0.0487

0.0143

0.0018

0.0010

0.0024

0.0048

0.0030

0.0031

0.0035

**Table 3.** The ratio of peptide-ARP over glycine-ARP and ratio between diglycine-ARP and triglycine-ARP under different initial pH and temperature in relative reactivity analysis
	pH 3	pH 5	pH 7	pH 9
*1H and 2H means thermal treatment of 1 hour and 2 hours, receptivity.
80 °C 1H	1.21	0.78	1.06	0.96	1.96	0.97	0.08	0.15
80 °C 2H	1.01	1.32	0.98	1.00	1.40	0.88	0.08	0.17
100 °C 1H	0.96	0.82	1.44	0.80	2.33	0.43	0.08	0.13
100 °C 2H	0.96	0.87	0.92	0.90	1.30	0.53	0.08	0.09
130 °C 1H	0.83	0.89	0.51	0.59	0.32	0.96	0.54	0.98
130 °C 2H	0.75	0.52	0.28	0.81	0.35	0.95	0.57	1.14
160 °C 1H	0.96	0.40	0.38	0.04	0.93	0.17	1.15	0.40
160 °C 2H	0.97	0.92	0.13	0.03	0.20	0.02	0.32	0.05
*1H and 2H means thermal treatment of 1 hour and 2 hours, receptivity.
80 °C 1H	1.6	1.1	2.0	0.6
80 °C 2H	0.8	1.0	1.6	0.5
100 °C 1H	1.2	1.8	5.4	0.6
100 °C 2H	1.1	1.0	2.4	0.9
130 °C 1H	0.9	0.9	0.3	0.5
130 °C 2H	1.5	0.3	0.4	0.5
160 °C 1H	2.4	8.5	5.6	4.4
160 °C 2H	1.1	4.4	11.8	6.6

Table 3. The ratio of peptide-ARP over glycine-ARP and ratio between diglycine-ARP and triglycine-ARP under different initial pH and temperature in relative reactivity analysis

pH 3

pH 5

pH 7

pH 9

DA/GA

TA/GA

DA/GA

TA/GA

DA/GA

TA/GA

DA/GA

TA/GA

*1H and 2H means thermal treatment of 1 hour and 2 hours, receptivity.

80 °C 1H

1.21

0.78

1.06

0.96

1.96

0.97

0.08

0.15

80 °C 2H

1.01

1.32

0.98

1.00

1.40

0.88

0.08

0.17

100 °C 1H

0.96

0.82

1.44

0.80

2.33

0.43

0.08

0.13

100 °C 2H

0.96

0.87

0.92

0.90

1.30

0.53

0.08

0.09

130 °C 1H

0.83

0.89

0.51

0.59

0.32

0.96

0.54

0.98

130 °C 2H

0.75

0.52

0.28

0.81

0.35

0.95

0.57

1.14

160 °C 1H

0.96

0.40

0.38

0.04

0.93

0.17

1.15

0.40

160 °C 2H

0.97

0.92

0.13

0.03

0.20

0.02

0.32

0.05

pH 3

pH 5

pH 7

pH 9

DA/TA

*1H and 2H means thermal treatment of 1 hour and 2 hours, receptivity.

80 °C 1H

1.6

1.1

2.0

0.6

80 °C 2H

0.8

1.0

1.6

0.5

100 °C 1H

1.2

1.8

5.4

0.6

100 °C 2H

1.1

1.0

2.4

0.9

130 °C 1H

0.9

0.3

0.5

130 °C 2H

1.5

0.3

0.4

0.5

160 °C 1H

2.4

8.5

5.6

4.4

160 °C 2H

1.1

4.4

11.8

6.6