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Figure 6.2.11 Relationships of weight gains to percent of L- and D- Trp isomers in amino acid diets fed to mice. Adapted from References 13, 62, and 63.
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6.2.3.2.2 D-Arginine Both L- and D-Arg protected against oxygen-radicalinduced injury of rat heart tissue (67) and against endotoxin shock in rabbits (68). D-Arg and other D-amino acids inhibited cell proliferation and tumor growth in rats (69), acted as a central nervous system stimulant, and exhibited anticonvulsant activity in humans (70). A D-Arg-containing peptide protected young chicks against memory loss (71). These observations suggest that dietary D-Arg may bene t human health. 6.2.3.2.3 D-Aspartic Acid D-Asp aggravated the pyelonephritis in rats induced by Staphylococcus aureus bacteria (72). Because D-Asp also prevented potassium and magnesium depletion in rats induced by cardiac drugs and diuretics (73), it may be of bene t to cardiac patients. 6.2.3.2.4 D-Cysteine Although L-CysSH had a sparing effect of L-Met consumed by mice, D-CysSH did not (14). In fact, D-CysSH imposed a metabolic burden as indicated by depressed growth when fed to mice with less than optimal levels of D-Met. The 24% decrease in weight gain of the D-CysSH plus L-Met amino-acid diet compared with L-Me alone implies that D-Cys is nutritionally antagonistic or toxic. D-CysSH but not N-acetyl-D-cysteine lowered rat blood cyanide levels derived from acrylonitrile (21, 74, 75). D-CysSH is also reported to be involved in the detoxi cation and/or prevention of toxicities caused by other cyanides (76), the drug paracetamol (77), and other drugs (78 80). L-Cysteineglutathione disul de but not the D-cysteine analog protected mice against acetaminophen-induced liver damage (81). 6.2.3.2.5 D-Cystine Although L-Cys is not an essential amino acid for rodents, less L-Met is needed for growth if the diet contains L-Cys (14). Our
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DIETARY SIGNIFICANCE OF PROCESSING-INDUCED D-AMINO ACIDS
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results show that L-Cys is somewhat more ef cient in sparing D-Met than in sparing L-Met in diets containing low levels (0.29%) of the two isomers. Supplementation of D-Met with an equal sulfur equivalent of L-Cys doubled growth. Thus, the overall response was equal to that produced by L-Met in the presence of L-Cys. In contrast, supplementation of suboptimal levels of L-Met with increasing concentrations of D-Cys reduced the growth rate of mice. These results imply that excess D-Cys in the diet is toxic. 6.2.3.2.6 D-Histidine D-His enhanced zinc accumulation, but reduced the fraction of zinc that was retained and absorbed by sh (82). Both D- and L-His enhanced the DNA degradation by hydrogen peroxide and ferric ions (83). D-His-induced cell injury is mediated by an iron-dependent formation of reactive oxygen species (84, 85). These observations suggest that D-His may be toxic to humans. 6.2.3.2.7 Lanthionine (LAN) Isomers LAN isomers and other D-amino acids are formed during the biosynthesis of microbial-derived peptide antibiotics (86 90) and during exposure of proteins to alkali and heat. Reaction of the SH group of CysSH and the double bond of dehydroalanine gives rise to one pair of optically active D- and L-isomers and one diastereomeric (meso) form of LAN (21). The mixture of DL + meso-LAN has a sparing effect on L-Met, as evidenced by a 27% greater weight gain when the two amino acids were fed together, than when fed suboptimal L-Met (14, 15). 6.2.3.2.8 D-Lysine In contrast to sulfur-containing amino acids, D-Lys is not utilized as a nutritional source of L-Lys by chicks, dogs, mice, rats, or humans, presumably because D-amino oxidase does not metabolize D-Lys. Because of its low toxicity, D-Lys may be a better candidate to reduce radioactivity uptake by the kidneys during cancer therapy with radionuclides than is L-Lys (91 93). 6.2.3.2.9 Lysinoalanine (LAL) Isomers The amino acid LAL, formed concurrently with D-amino acids in alkali-treated proteins, has two asymmetric C-atoms, making possible four separate diastereoisomeric forms: DD, DL, LD, and LL. The nutritional value of the individual LAL isomers as a source of L-Lys is not known. Table 6.2.3 shows that a mixture of LL and LD isomers has a nutritional value for the mouse equivalent on a molar basis to 3.8% of L-Lys. For comparison, the table also lists the nutritional values of other Damino acids we determined. The four LAL isomers differ in their ability to chelate metal ions such as copper (94). The transformation of even a small fraction of L-Lys to D-Lys and to LAL adversely affects the nutritional quality of cereal proteins to a greater extent than would be the case for legume (soy) and animal (casein) proteins, whose L-Lys content is much higher (4, 95, 96).
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