Food Biochemistry and Food Processing (2 edition)

BLBS102-c10 BLBS102-Simpson March 21, 2012 13:7 Trim: 276mm X 219mm Printer Name: Yet to Come

210 Part 2: Biotechnology and Enzymology

H

N

N

H

N

N

N

N

H

N

N N

HO N

H

HN

O

NH

HOH

HO

H

R

N

H

HN N N+

H

Glucosepane Pentosidine

+

GOLA Vesperlysine A (LM-1)

Protein backbone

R = H = GODIC

R = CH 3 = MODIC

R = CH = DODIC

2

H OH

H OH

CH 2 OH

N

R N

R=CH 3 = MOLD

R=H GOLD=

+

H N

HO

H

+

H

NH

Lys-hydroxy-triosidine

NH

N

HO

HO

HO

+ +

HO

OH

OH

Threosidine

N

NH

N

+

H

HO

H H

H

N

Arg-hydroxy-triosidine

N

H

NH

OH

O

N

N OH

HN OH

NH 2

O

ALI

Figure 10.2.A selection of known protein cross-links derived from the Maillard reaction in the body, from Miller and Gerrard (2004). (Sell and

Monnier 1989, Nakamura et al. 1997, Prabhakaram et al. 1997, Brinkmann-Frye et al. 1998, Lederer and Buhler 1999, Lederer and Klaiber

1999, Al-Abed and Bucala 2000, Glomb and Pfahler 2001, Biemel et al. 2002 Tessier et al. 2003). The extent to which these cross-links are

present in food is largely undetermined. GOLA,N^6 - {2-[(5-amino-5-carboxypentyl)amino]-2-oxoethyl}lysine; ALI, arginine–lysine imidazole;

GODIC,N^6 -(2-{[(4S)-4-ammonio-5-oxido-5-oxopentyl]amino}-3,5-dihydro-4H-imidazol-4-ylidene)-L-lysinate; MODIC,N^6 -(2-{[(4S)-4-

ammonio-5-oxido-5-oxopentyl]amino}-5-methyl-3,5-dihydro-4H-imidazol-4-ylidene)-L-lysinate; DOGDIC,N^6 - {2-{[(4S)-4-ammonio-5-oxido-

5-oxopentyl]amino}-5[(2S,3R)-2,3,4-trihydroxybutyl]-3,5-dihydro-4H-imidazol-4-ylidene)-L-lysinate; MOLD, methylglyoxal lysine dimer; GOLD,

glyoxal lysine dimer.