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ABSTRACT variation in the distribution ofdietary nitro- these calculations, and to apply the computerized calculations
gen among the different amino acids is one factor that can mod- to a variety ofmixtures ofamino acids and other foods.
ify the calorie equivalent per weight of amino acid or protein.
770 Am iC/in Nutr l990;52:770-6. Printed in USA. 1990 American Society for Clinical Nutrition
CALORIE CONTENT OF FREE AMINO ACIDS 771
(H02), and the ratio of gaseous carbon dioxide produced to 8) Sulfur amino acids require additional algebraic terms to
oxygen consumed (RQ) also depend on the distribution of account for energy release and oxygen utilization in oxidation
urine nitrogen among the possible metabolites. METENERG ofsulfur to sulfate and the small change in apparent molecular
computes these quantities for each amino acid after the urine- composition ofunnary nitrogenous compounds occasioned by
nitrogen distribution is specified according to the following the excretion of taurine.
computational algorithm: The above algorithm is not original (5), but the algebraic for-
1) The heat of combustion of urinary nitrogenous corn- mulation of the chemical balance allows the computerization
pounds is computed per mole urine nitrogen by the expression of the calculations, with easy extension of the calculations to
any specified distribution of urinary nitrogenous compounds.
: (F1,).(HJn1) The ionization fraction of organic acids is required to obtain
correct RQ values (5), and the program includes input of the
where F, is the fraction of urine nitrogen in compound i, H,
ionization fraction and the RQ correction for five common
is the heat ofcombustion ofcompound i, and n is the number
short-chain carboxylic acids.
of moles nitrogen per mole i; i represents any urinary corn-
7) The ratio of oxygen utilization to urine nitrogen produc- the latter 18 substrates were obtained from published literature
(2). The program is supplied with two parameter files; one con-
tion (L 02:g N) is
tains compositions and molecular weights of amino acids
O:N = X.gasconstant/14.0067.n5 (MOLECULE.MW) and the other contains compositions and
772 MAY AND HILL
TABLE 1
Heats ofcombustion and biologic oxidation ofamino acids
Metabolizable energy5
kca//g kca//g(kJ/g)
Alanine 4.34 1 3.425 ( 13.70) 3.549 ( 14.20) 3.494 ( 13.98) 4.369 ( I 8.28)
Arginine S. 129 3.254 ( 13.02) 3.508 ( 14.03) 3.396 ( 13.58) 3.784 ( I 5.83)
Asparagine 3.488 2.252 (9.0 1) 2.4 19 (9.68) 2.345 (9.38) 2.7 18 ( 1 1.37)
Aspartic acid 2.875 2.26 1 (9.04) 2.344 (9.38) 2.307 (9.23) 2.689 ( 1 1.25)
Cysteine 3.256 4.3 12 ( 17.24) 4.402 ( 17.6 1 ) 4.362 ( 17.44) 4.792 (20.05)
Cystine 3.0 15 4.093 ( 16.37) 4. 182 ( 16.73) 4. 143 ( 16.57) -
Phenylalanine 6.723 6.229 (24.92) 6.296 (25. 18) 6.266 (25.06) 7.036 (29.44)
Proline 5.681 4.970(19.88) 5.066(20.27) 5.024(20.10) 5.937(24.84)
Serine 3.308 2.532 ( 10. 13) 2.637 ( 10.54) 2.590 ( 10.36) 3. 107 (13.00)
Threonine 4.120 3.434(13.74) 3.527(14.11) 3.486(13.94) 4.101 (17.16)
Tryptophan 6.588 5.787(23.14) 5.896(23.58) 5.848(23.39) 6.419(26.86)
Tyrosine 5.859 5.409 (2 1.64) 5.470 (2 1.88) 5.443 (2 1.77) 6.039 (25.27)
Valine 5.963 5.264 (2 1.06) 5.358 (2 1.43) 5.3 16 (2 1.27) 6.276(26.26)
I 4.781 4.136(16.54) 4.253(17.01) 4.201 (16.80) 4.847 (20.28)
SD 1.324 1.342(5.370) 1.321 (5.283) 1.339(5.321) 1.530(6.402)
CV(%) 27.7 32.4 31.1 31.7
a For four distributions ofurine nitrogen: set 1-90% urea, 3% ammonia, 5% creatinine, 2% uric acid; set 2-100% ammonia; set 3-l00% urea;
and set 4-data from Table 3 ofreference (2) for 100% urea.
formula weights ofthe acyl portion (dehydrated) ofthe amino product. Minor differences would be expected from the use of
acids (MOLECULE.FW). Selection of parameter files is ac- slightly different primary sources, but the large differences in
complished by the DOS batch files. The program as written is our calculations and those previously reported was bother-
appropriate for diets composed of modular components (pro-. some. We replicated the numbers of Livesey and Elia by use of
tein and/or amino acids, carbohydrate, fats), and extension to the compositions ofthe acyl portion for computation of nitro-
natural diets would require modification or assumption
that gen content and formula weights rather than the molecular
the nonprotein nitrogen was negligible in quantity.
corn- The composition for each ofthe amino acids. That is, the previously
putations strictly apply to the portion of the diet that is ab- reported parameter values refer to amino acids in protein when
sorbed or taken parenterally; digestibility is not specifically en- the amino acid data has been expressed as
tered in the program. Because the user is prompted for the diet
components by weight, known digestibility factors (amount ab- Amount ofamino acid = fraction ofprotein nitrogen
sorbed/amount eaten) can be accounted for by entering Weight
in amino acid X acyl formula weight per mole nitrogen
x Digestibility instead ofWeight for each nutritive component
and entering Weight X (1-Digestibility) plus the weight of Ifamino acid composition is expressed in these terms, the sum
dietary minerals as Mineral for the program-this allows cor- of amino acid weights will be equivalent to the protein weight
rect energy computations per weight of the original diet. (The and we can call this mode of expression protein equivalent.
compiled program is available from the authors for $25 (US) Actually, the sum ofamino acid weights obtained by hydrolysis
to cover reproduction and shipping.) of protein will be greater than the weight of the initial protein
by the amount ofwater added to hydrolyze the peptide bonds.
Results and discussion There is no convention stated for expression of amino acid
data in standard tables of food composition (6). Furthermore,
Table 1 shows the heats of combustion and metabolizable the protein-equivalent mode ofexpression ofamino acid corn-
energy for amino acids. Metabolizable energy is presented for position ofproteins is not applicable to diets composed of crys-
four distributions of urine nitrogen. The right-hand column of talline amino acids, as are often used in experiments and in
Table 1 is the metabolizable energy reported by Livesey and parenteral nutrition. The previously published values for me-
Elia (5) under the assumption that urea is the sole urinary end tabolizable energy of amino acids do not apply to diets corn-
CALORIE CONTENT OF FREE AMINO ACIDS 773
TABLE 2 g protein equivalent and not per g free amino acid (7). This
Heat equivalent ofoxygen for amino acids communication is in agreement with the findings ofthis paper.
These data are ofinterest for two reasons: the design of isoca-
Heat equivalen t ofoxygen consum ed in oxidation5
loric, isonitrogenous research and therapeutic diets requires
Amino acid Set 1 Set 2 Set 3 these computations ifthe distribution ofamino acids is atypi-
cal, and the measurement ofenergy expenditure and substrate
kcal/L (ki/L) oxidation rates by indirect calorimetry or measurement of en-
ergy expenditure in free-living subjects by doubly labeled water
Alanine 4.627 ( I 8.5 1 ) 4.703 ( 18.8 1) 4.630(18.52)
Arginine 4.799 ( I 9. 19) 4.957 ( 19.83) 4.798 (19.19) require proper values of 0:N, H02, and RQ for accuracy.
Asparagine 4.600 (1 8.40) 4.753 (19.0 1) 4.607(18.43) Table 5 shows the effect ofapplying these values to the compu-
Aspartic acid 4.563 ( 18.25) 4.640 ( 18.56) 4.567 (18.27) tation ofthe biologic energy content ofseveral amino acid mix-
Cysteine 5.318 (21.27) 5.359 (21.44) 5.31 1 (21.24) tures. variation in amino acid composition results in different
Cystine 5.308 (2 1.23) 5.350 (2 1.40) .300 (21.20) energy contents despite similar weight percentages of total
Glutamic acid 4.567 ( 18.27) 4.6 18 ( 18.47) 4.70(18.28)
Aminoacid Setl Set2 Set3 3, O:N is highly variable among the natural amino acids. A
problematic but critical question is whether the mix of amino
L/L acids being oxidized is the same under all conditions or among
Alanine 0.835 1.000 0.833 all subjects in a research study. Computation of a correction
Arginine 0.727 1.091 0.727 for urine nitrogen from the dietary amino acid composition
Asparagine 1.011 1.333 1.000 implies the assumption that urine nitrogen is derived from
Asparticacid 1.175 1.333 1.167 amino acids in the same relative proportions as in the diet. This
Cysteine 0.554 0.667 0.556 assumption may be true in a steady state in adult humans or
bution ofwhole body protein or that dispensable amino acids mation ofamino acids and related compounds. In: Sober HA, ed.
are oxidized in preference to indispensable amino acids, would Handbook ofbiochemistry. 2nd ed. Cleveland: CRC Press, 1970:
result in computation of different values for 0:N . Errors in B62-4.
3. Dean JA, ed. Langes handbook ofchemistry. 13th ed. New York:
estimating protein oxidation from end products ofamino acid
McGraw-Hill, 1985.
metabolism can affect the estimates ofrates ofoxidation of car-
4. Diem K, Lentner C, eds. Scientific tables. 7th ed. Ardsley: Ciba-
bohydrate and fat and of total energy expenditure obtained
Geigy Corp 1975:663-72.
from indirect calorimetry (5). Determination ofthe oxidation S. Livesey G, Elia M. Estimation ofenergy expenditure, net carbohy-
rates of multiple amino acids simultaneously is technically drate utilization, and net fat oxidation and synthesis by indirect
difficult because of the limited number of tracers for the corn- calorimetry: evaluation of errors with special reference to the de-
mon end product carbon dioxide. METENERG allows corn- tailed composition offuels. Am J Clin Nutr l988;47:608-28.
putation ofbounds ofvalues ofO:N and Heq for differing as- 6. Consumer and Food Economic Institute. Composition of foods:
sumed proportions ofamino acids. dairy and egg products. Agricultural handbook no. 8-1. Washing-
An alternative technique for measurement of energy expen- ton, DC: USGovernment PnntingOffice, 1976.
7. Erratum. Am J Clin Nutr l989;50:l475.
research diets will require application of the individual energy ofcombustion oflysine is not tabulated but can be calcu-
parameters rather than assumption of constant values for all lated from the heat of formation. The heat offormation is
the enthalpy change for the reaction
amino acids. We are making METENERG available for this
purpose. El
6C+ 7 H2 +02 + N2-C6H14N202
I. Widdowson EM. Note on the calculation of the energy value of C6H 14N202 + 02 #{248}6 CO2 + 7 H2O + N2
foods and of diets. In: Paul AA, Southgate DA, eds. The composi-
tion of foods. 4th ed. New York: Elsevier/North-Holland Biomedi- The summation reaction
cal Press, 1978:322-6.
2. Hutchens JO. Heat of combustion, enthalpy and free energy of for- 6C+7H2+02+N2-.+6C02+7H2O+N2
776 MAY AND HILL
has an enthalpy that is a sum of heats of formation of the
Because food items are usually specified by weight, we con-
products, ie, vert this result by division by the molecular weight of lysine
(146.19) to 4.933 kcal/g.
(Heat of formation)L, + (heat of combustion)L5
6) The CO2 produced by oxidation of lysine is
= 6 X (heat of formation)co2 + 7 X (heat of formation)H20
(6 - 0.5167 X 2) mol/mol LYS = 4.9667 mol/mol LYS
Substituting the known values for heats of formation, we 7) The H2O produced by oxidation of lysine is
get
(14 - 2.0667 X 2)/2 mol/mol LYS = 4.9333 mol/mol LYS
(Heat of combustion)L, = [6 X 94.38 + 7 X 68.38
8) The oxygen consumed in catabolism of lysine is
- 162.2] kcal/mol = 882.7 kcal/mol
(2 X 4.9667 + 4.9333 + 0.4667 x 2
5) The metabolizable energy is the heat of combustion minus
the heat of combustion of urinary products, ie, - 2)/2 mol/mol LYS = 6.9000 mol/mol LYS.