THE

cr-KEJTO ANALOGUES
AND
BY

(From the National

OF ARGININE,
LYSINE

ALTON

ORNITHINE,

MEISTER

Cancer Institute, National

Bethesda, Maryland)

(Received for publication,

Institutes

of

Health,

August 6, 1953)

acids, or their w-N-carbobenzoxy

derivatives,
resulted
in the formation
of
pipecolic
acid and proline,
respectively,
a finding compatible
mith the ex-

pected tendency to cyclization.

EXPERIMENTAL

Methods-Arginase (7), arginine decarboxylase (8),l lysine decarboxylase

(9),* and ornithine decarboxylase (lO)l were prepared as described.
Ascending paper chromatographic studies on Whatman No. 4 paper were
1 Cultures of the organisms possessing specific decarboxylase
tained through the courtesy of Dr. E. F. Gale.
577

activity

were ob-

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Although the cr-keto analogues of most of the common natural amino

acids have been prepared, there are apparently no reports describing the
preparation of the cr-keto acids corresponding to arginine (or-ketod-guanidinovaleric acid), ornithine (oc-keto-&aminovaleric acid), and lysine (CXketo-e-aminocaproic acid). The 2,4-dinitrophenylhydrazones
of ac-keto-daminovaleric (l-3) and cr-keto-&guanidinovaleric (4) acids have been
isolated; however, the free acids were not obtained. In the present communication the preparation of ar-keto-6-guanidinovaleric acid, as well as
a-keto-&nitroguanidinovaleric
acid, by enzymatic oxidative deamination
(5) of the corresponding L-amino acids is described.
Since lysine and ornithine were oxidized relatively slowly, the cr-keto
acids corresponding to these amino acids were therefore obtained as the
w-N-carbobenzoxy derivatives, by enzymatic oxidation of the more susceptible w-N-carbobenzoxyamino acids. The carbobenzoxy groups were then
removed from the resulting cr-keto acids by treatment with hydrobromic
acid in acetic acid solution (6), yielding the hydrobromides of the desired
compounds. The a-keto analogues of lysine and ornithine would be expected to exhibit tendency to cyclize by condensation of the cY-keto and
w-amino groups. However, the properties of the keto analogues of lysine
and ornithine include ability to form 2,4-dinitrophenylhydrazones,
decarboxylation with hydrogen peroxide to the corresponding w-amino acids,
and non-enzymatic transamination with pyridoxamine to form lysine and
ornithine, respectively.
On the other hand, hydrogenation of these keto

578

a-KETO

ANALOGUES

2 The author is indebted to Dr. B. D. Davis for cultures of the E. coli mutants
used in this study.
3 About 80 per cent of the oxidase activity was recovered after lyophilization
of
the contents of the dialysis sac.
4 The microanalyses reported in this paper were performed by Mr. R. J. Koegel
and Dr. W. C. Alford.

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carried out with the solvent mixtures used previously

(ll), as well as with
a solvent consisting of methanol, water, and pyridine (80 : 20 : 4) (12).
Microbiological
procedures were performed as described by Davis and
Mingioli (13) ?
Lu-Keto-&guanidinovaleric
Acid-2
gm. of L-arginine hydrochloride
were
oxidatively
deaminated with 300 mg. of dialyzed Crotalus adamanteus
venom in the presence of crystalline catalase.
The procedure was similar
to that previously
described (5), except that the ion exchange step was
omitted.
When oxidation was complete, the solution was dialyzed against
two changes of distilled water and the combined dialysates were evaporated
in vacua to about 15 CC.~ The free a-keto acid crystallized as the monohydrate on cooling.
After recrystallization
from hot mater, the yield of
pure material was 1.3 gm. (72 per cent).
The product darkened at 221
but did not melt when heated to 250. The keto acid gave a positive
Sakaguchi test (14). Calculated for CsHn03N3.H20,
C 37.7, H 6.9, N
22.0; found, C 37.8, H 6.9, N 21.8 per cent.4 The acid gave an immediate
crystalline precipitate on addition of 1 per cent 2,4-dinitrophenylhydrazine
in 2 N hydrochloric
acid. The hydrazone darkened at 218 but did not
melt when heated to 250; calculated for CLH1506NT*HzO,
C 38.8, H 4.6,
N 26.4; found, C 38.9, H 4.5, N 26.2 per cent. The flavianate was prepared by mixing concentrated
aqueous solutions containing equimolar
quantities of flavianic acid and the cY-keto acid. The resulting crystalline
product was recrystallized
from ethanol, and on analysis gave the following: calculated for C&,H1~011N&S, C 39.4, H 3.5, N 14.4, S 6.6; found, C
39.9, H 3.8, N 14.4, S 6.7 per cent.
or-Keto-&nitroguanidinovaleric
Acid4.4
gm. of L-nitroarginine,
prepared
according to Bergmann, Zervas, and Rinke (15), were oxidatively
deaminated with 1.2 gm. of venom as described (5). The free ol-keto acid was
isolated and crystallized from hot water; the yield of pure compound was
4.0 gm. (91 per cent); m.p. 160. Calculated for CsH1005N4, C 33.0, H
4.6, N 25.7; found, C 33.2, H 4.6, N 25.5 per cent. The corresponding
2,4-dinitrophenylhydrazone
(recrystallized
from glacial acetic acid) melted
at 225; calculated for G2H140sN~, C 36.2, H 3.6, N 28.1; found, C 36.0,
H 3.6, N 27.8 per cent.
Neither a-keto-&guanidinovaleric
acid nor cr- keto-&nitroguanidinovaleric acid was decarboxylated
by yeast carboxylase,
whereas both gave
equimolar quantities of carbon dioxide when treated with ceric sulfate (5)

A.

MEISTER

579

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or hydrogen peroxide (16). Both cr-keto-&guanidinovaleric

and oc-keto-bnitroguanidinovaleric
acids exhibited low activity in the lactic dehydrogenase system.
Under the conditions previously described (17), the rates
of reduction were 9.00 and 42.6 X lo-* mole per mg. of enzyme per minute, respectively.
(Rate for pyruvate = 26,800.)
Neither keto acid, nor
nitroarginine, was attacked by arginase or by arginine decarboxylase.
Non-enzymatic
transamination
between these keto acids and pyridoxamine yielding arginine and nitroarginine,
respectively, was demonstrated
as follows (18): Solutions containing 180 PM of keto acid, 60 ,~LM of pyridoxamine, and 0.4 pM of aluminum chloride in 0.4 cc. of 0.1 M sodium acetate
buffer (pH 4.9) were heated at 100 for 30 minutes.
Paper chromatographic study revealed formation of the corresponding
amino acids and
disappearance of approximately
half of the pyridoxamine.
In the experiment with a-keto-&guanidinovaleric
acid, 12.0 pM of L-arginine were formed
as determined with arginine decarboxylase.
a-Keto-6-N-carbobenzoxyvaleric
Acz&--6-N-Carbobenzoxy-n-ornithine
was
prepared by a procedure analogous to that of Neuberger and Sanger for the
corresponding
lysine derivative
(19). 5 gm. of &N-carbobenzoxy-r,-ornithine were oxidatively deaminated with 500 mg. of the venom preparation
(5). When the reaction was complete, the mixture was acidified to Congo
red paper with concentrated
hydrochloric
acid, and the solution was extracted with several portions of ethyl acetate.
The ethyl acetate extracts
were combined, dried over anhydrous sodium sulfate, and evaporated to a
thick oil, which, after repeated washing with petroleum ether, solidified on
standing at - 10 for 3 weeks.
The compound was crystallized from acetone-petroleum
ether; m.p. 121. The yield of pure material was 3.4 gm.
Calculated for C13H1505N, C 58.9, H 5.7, N 5.3; found,
(68 per cent).
C 58.6, H 5.6, N 5.2 per cent. The keto acid readily formed a 2,4dinitrophenylhydrazone
which, after recrystallization
from ethyl acetate,
melted at 194; calculated for C19H190sN5, C 51.2, H 4.3, N 15.7; found,
C 51.3, H 4.4, N 15.7 per cent.
cu-Keto-&aminovaleric Acid (A-Pyrroline-d-carboxylic
Acid)-Attempts
to
prepare a-keto-&aminovaleric
acid in pure form by catalytic hydrogenation
of the carbobenzoxyketo
acid (palladium black, 50 per cent methanol, 2
equivalents of hydrochloric
acid) were not successful.
Paper chromatographic study indicated that the hydrogenated material was a mixture, the
major component of which was identified as proline.
Removal of the carbobenzoxy group as described by Ben-Ishai and Berger (6) was carried out as follows: 100 mg. of cr-keto-d-N-carbobenzoxyvaleric acid were mixed with 0.5 cc. of glacial acetic acid saturated with
hydrogen bromide at 22-26.
After standing at this temperature
for 30
minutes with occasional shaking, carbon dioxide evolution had ceased, and

580

oc-KETO ANALOGUES

5 The product became yellow and liquefied when exposed to the air at room temperature for several hours. The instability
of the compound may be due to polyVogel and Davis (20) observed that Al-pyrroline-5-carboxylic
acid apmerization.
parently polymerizes readily, a property which prevented isolation of this compound
in pure form.
6 Stoichiometric
decarboxylation
was observed with freshly prepared solutions,
and with solutions of the products in 0.1 N hydrochloric acid, 0.1 N sodium hydroxide,
and 0.1 M phosphate buffer (pH 7.5), which were allowed to stand at 37 for 5 hours
prior to decarboxylation.
7 Under these conditions,
glutamic-r-semialdehyde
(Al-pyrroline-5-carboxylic
acid) yielded glutamic acid and no carbon dioxide.

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15 cc. of dry ether were added yielding 50 mg. of a white crystalline precipitate. This was washed thoroughly with dry ether and placed in vacua
over phosphorus pentoxide and sodium hydroxide.
On analysis the following values were obtained: C 30.6, H 4.4, N 7.2, Br 41.0 per cent. These
data agree with the composition of the hydrobromide of A-pyrroline-2carboxylic acid (calculated for GH~02N*HBr, C 30.9, H 4.1, N 7.2, Br 41.2
per cent). The product became yellow when heated to 118 and decomposed at 136.5 Several properties of the product were investigated: (a)
The addition of a a-fold excessof 1 per cent 2,4-dinitrophenylhydrazine
in
2 N hydrochloric acid to a solution of 50 mg. of the product in 1 cc. of
water resulted in immediate precipitation of a crystalline hydrazone. On
recrystallization from hot water 40 mg. were obtained, with a melting
point of 211-212 (N, calculated for CUH~~O~N~,22.5; found, 22.4 per
cent). The hydrazone did not contain inorganic halogen. The hydrochloride of the 2,4-dinitrophenylhydrazone
of cr-keto-&aminovaleric acid
was prepared as described by Krebs (1) by oxidation of nn-proline with
n-amino acid oxidase. A slight excessof aniline was added to an ethanolic
solution of the hydrazone hydrochloride, resulting in precipitation of the
free hydrazone. After crystallization from water, the melting point was
211-212O. A mixed melting point with the hydrazone prepared from the
product showed no depression. The paper chromatographic behavior of
the two hydrazones was identical. (b) The product gave stoichiometric
quantities of carbon dioxide when treated with ceric sulfate (5) or with
hydrogen peroxide (16).6 After treatment with hydrogen peroxide at pH
values of 2.5 or 7.5, y-aminobutyric acid formation was revealed by paper
chromatography and no glutamic acid was detected. (c) Solutions containing 160 PM of pyridoxamine, 40 PM of the product, and 2 PM of aluminum chloride in 2 cc. of 0.1 M sodium acetate buffer (pH 4.9) were
heated at 100 for 30 minutes. The solutions became markedly yellow
after 5 minutes of heating, suggesting formation of pyridoxal.
Ornithine
formation was revealed by paper chromatography, and assay with Escherichia coli, mutant 160-37, gave a value of 5.6 PM of n-ornithine.
(4
Hydrogenation of 108 j.6M of the product with platinum oxide catalyst (40

A.

MEISTER

581

* Prepared
(20) from r,r-dicarbethoxy-r-acetamidobutyraldehyde
generously
provided by Dr. H. J. Vogel.
9 The RF values
for the o-aminobenzaldehyde
compounds
formed
from Al-pyrroline-5-carboxylic
acid, Ai-pyrroline-2-carboxylic
acid, and A-piperidine-2-carboxyto 0.69, and 0.70 to 0.75,
lit acid, with the pyridine
solvent
(la), were 0.55 to 0.60,0.64
respectively.
The corresponding
values
obtained
with
chromatograms
developed
with 77 per cent ethanol
were 0.55 to 0.61, 0.62 to 0.68, and 0.71 to 0.76.
When 0.1 M
potassium
phosphate
buffer
(pH 7.5) was used as the solvent,
the Rp values
were
0.75 to 0.80,0.83
to 0.87, and 0.79 to 0.83.
In tert-amyl
alcohol
saturated
with phthalate buffer
(21), the Rp value for the Ai-piperidine-2-carboxylic
acid compound
was
0.42 to 0.45, and that for the Ai-pyrroline-2-carboxylic
acid product
was 0.28 to 0.32.
The spot corresponding
to the Ai-pyrroline-5-carboxylic
acid derivative
gradually
faded and ultimately
disappeared
during
chromatography
with this solvent.

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pounds pressure, 22-26, 18 hours) yielded a solution containing 29.8 /IM

of L-proline, as determined with E. coli, mutant 55-l.
(e) The product did
not support the growth of E. coli, mutants 55-l (which responds to L-proline), 55-25 (which responds to L-proline or Al-pyrroline-5-carboxylic
acid),
or 160-37 (which responds to L-ornithine, L-arginine, or L-citrulline).
(f)
The product was not reduced by lactic dehydrogenase,
nor was it decarboxylated by ornithine decarboxylase.
(g) The product gave a yellow
color on addition of o-aminobenzaldehyde
at pH 7.5. The compound
formed (presumably
the dihydroquinazolinium
derivative
formed by
condensation of o-aminobenzaldehyde
and Al-pyrroline-2-carboxylic
acid)
was distinguished from that obtained from Al-pyrroline-5-carboxylic
acid8
by paper chromatography.g
ar-Keto-e-N-carbobenzoxycaproic
Acid-This
keto acid was obtained by enzymatic oxidation of 5 gm. of e-N-carbobenzoxy-L-lysine
(19), as described
above for the corresponding
ornithine derivative.
The compound crystallized on standing overnight at -10 and was recrystallized
from ethyl
acetate-petroleum
ether; m.p. 109. The yield was 3.8 gm. (76 per cent).
Calculated for C~~H~~OSN, C 60.2, H 6.1, N 5.0; found, C 60.0, H 6.4, N
5.0 per cent. The 2,4-dinitrophenylhydrazone
of this keto acid (recrystallized from ethyl acetate) melted at 160. Calculated for CzoHzlOgNs,
C 52.3, H 4.6, N 15.2; found, C 52.5, H 5.0, N 15.2 per cent.
cY-Keto+aminocaproic
Acid (Al-Pipe&line-d-carboxylic
A&)-Catalytic
hydrogenation
of cY-keto+N-carbobenzoxycaproic
acid was carried out
with palladium black (80 per cent methanol, 2 equivalents of hydrochloric
acid). After hydrogenation,
the solution was evaporated to dryness in
vacua. The residue was crystallized twice from ethanol-benzene,
yielding
m,-pipecolic acid hydrochloride
in 80 per cent yield; m.p. 264. Calculated for CsHrlOzN*HCl,
C 43.5, H 7.3, N 8.5, Cl 21.4; found, C 43.3, H
7.3, N 8.5, Cl 21.5 per cent. The chromatographic
behavior and the
infra-red absorption curves (Nujol mull) of this compound and a sample
of nn-pipecolic acid hydrochloride
prepared by catalytic hydrogenation
of

582

a-KETO

ANALOGUES

DISCUSSION

The compound obtained by treatment

of cr-keto-6-N-carbobenzoxyvaleric acid with hydrogen bromide gave elementary
analyses consistent

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picolinic acid hydrochloride

(22) were identical.
A mixed melting point
showed no depression.
Removal of the carbobenzoxy group was also carried out as follows: 250
mg. of a-keto+N-carbobenzoxycaproic
acid were mixed with 1 cc. of glacial
acetic acid saturated with hydrogen bromide, and allowed to stand at 2226 for 1 hour, at which time evolution of carbon dioxide was complete
and a white crystalline precipitate formed.
On addition of 50 cc. of dry
ether, further precipitation occurred.
The product was recrystallized
from
ethanol by addition of ether; yield 160 mg. (79 per cent).
Analyses of the
product agreed with the composition
of the hydrobromide
of cr-keto-eaminocaproic acid or that of the monohydrate
of the corresponding
cyclic
derivative, Al-piperidine-2-carboxylic
acid. Calculated for GH110zN*HBr,
C 31.9, H 5.3, N 6.2, Br 35.4; found, C 32.0, H 4.7, N 6.3, Br 35.5 per
cent; m.p. 192. The product was not deliquescent, and preparations
of
this compound were stable when stored at room temperature
for several
months.
However, when the compound was heated in vacua at 78 or 100
for 6 hours, decomposition was noted.
The product exhibited the following properties: (a) The addition of a 2-fold excess of 1 per cent 2,4-dinitroacid to 0.5 cc. of an aqueous solution
phenylhydrazine
in 2 N hydrochloric
containing 150 mg. of the acid resulted in the precipitation of a hydrazone
after standing at 22-28 for 3 days.
The hydrazone, which weighed 35
mg., was recrystallized
from hot water; m.p. 212. N, calculated for
C12H1506N5, 21.5; found 21.2 per cent. (b) On treatment of the product
with ceric sulfate or hydrogen peroxide, an equimolar quantity of carbon
dioxide was evolved,6 and &aminovaleric
acid was identified by paper
chromatography
after decarboxylation
with hydrogen peroxide at pH 2, 5,
and 7.5. No a-aminoadipic acid was formed under these conditions.
(c)
Non-enzymatic
transamination
yielding lysine was carried out as follows:
20 pM of the acid, and 1.6
Solutions containing 1200 pM of pyridoxamine,
PM of aluminum
chloride in 1.6 cc. of 0.1 M sodium acetate buffer at pH
5.5 were heated at 100. After 60 minutes of heating, 3.19 PM of L-lysine
were formed as determined with lysine decarboxylase.
(d) The product
was hydrogenated
in aqueous solution with platinum oxide catalyst (40
pounds pressure, 22-26, 18 hours).
Paper chromatograms
revealed the
formation
of pipecolic acid as the major product, and relatively small
amounts of cr-hydroxy-e-aminocaproic
acid. (e) The product did not support the growth of E. coli, mutant 26-26, which responds to L-lysine, nor
was it attacked by lactic dehydrogenase or lysine decarboxylase.
(f) The
compound gave a yellow color on addition of o-aminobenzaldehyde.g

A.

583

MEISTER

with Al-pyrroline-2-carboxylic
acid, and yielded proline on hydrogenation.
However, the product possessed properties characteristic
of ar-keto acids,
including hydrazone formation, decarboxylation
by hydrogen peroxide, and
conversion to ornithine by transamination.
The corresponding
lysine derivative
exhibited similar chemical behavior, although the elementary
analysis of this compound agreed with that calculated for oc-keto-e-aminocaproic acid, as well as the monohydrate
of A-piperidine-2-carboxylic
acid.
Treatment of both compounds with hydrogen peroxide at pH 7.5 yielded
the corresponding w-amino acids, and at the same pH value both compounds

k
c=o

COOH

/Y
CH2
I

CHz

\N/

CH2
I
C-COOH

CH2NH,
I

(C&h
C=O

CHZ-CH2
I
I
% CHZ
C-COOH
\N//

COOH

reacted with o-aminobenzaldehyde. The findings suggest that these compounds may react both as free cr-keto acids and as cyclic compounds.10
The properties of the ar-keto analogues of lysine and ornithine appear
analogous to those observed with glutamic-y-semialdehyde and other yaminoaldehydes, which have been shown to undergo spontaneous cyclization which is reversible under certain conditions (20, 23, 24).
ar-Keto-Saminovaleric acid has been identified by isolation as the 2,4dinitrophenylhydrazone as a product of n-proline and n-ornithine oxidation by sheep kidney n-amino acid oxidase (l), and as a product of the
oxidation of n-proline by rat kidney n-amino acid oxidase (2) .I2 In certain
systems n-proline is oxidized to glutamic-r-semialdehyde (3, ZS), which is
known to cyclize to Al-pyrroline-5-carboxylic
acid (20). The latter compound may be distinguished from Al-pyrroline-2-carboxylic
acid by assay
with E. COG,mutant 55-25, which responds only to Al-pyrroline-5-carboxy10 It is possible that other tautomeric forms exist such as the enolic form of the
normal chain compounds and the AZ cyclic forms, etc.
11 Oxidation of n-kynurenine
by rattlesnake venom in the presence of catalase
yielded kynurenic acid. In this instance cyclization is apparently not reversible,
owing to the formation of a stable aromatic ring. Oxidation in the absence of catalase resulted in the liberation of 1 mole of carbon dioxide, a finding compatible with
the intermediate
formation of o-aminobenzoylpyruvic
acid.
12n-Ornithine and n-lysine are susceptible substrates for rattlesnake n-amino acid
oxidase (25). We have found that oxidation of L-ornithine in the absence of catalase
was associated with the consumption of 1 mole of oxygen, formation of 1 mole each
of carbon dioxide and ammonia, and formation of r-aminobutyric
acid. The oxidation of L-lysine proceeded in a similar manner, and (in the absence of catalase)
b-aminovaleric
acid was formed.
After oxidation of these diamino acids in the
presence of catalase, the corresponding
o-keto acids were identified as the 2,4dinitrophenylhydrazones.

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CHzNHz
I
(CH&

584

a-KETO

ANALOGUES

lie acid. The evidence also indicates that these compounds give different
derivatives when condensed with o-aminobenzaldehyde.
Recent reports describe the presence of levorotatory
pipecolic acid in
certain plant tissues (27, 28). A possible mechanism of formation of this
amino acid from lysine may be considered in which oxidation or transamination of lysine is followed by cyclization of the resulting oc-keto-e-aminocaproic acid to Al-piperidine-2-carboxylic
acid, and optically specific reduction of the latter compound to the natural form of pipecolic acid. It is of
interest in this connection that Neurospora
cras.sa n-amino acid oxidase
oxidizes L-lysine to a product which yields nn-pipecolic acid after catalytic
hydrogenation
(29).

1. The preparation of the cr-keto analogues of arginine (cr-keto-d-guanidinovaleric acid) and nitroarginine
(a-keto-&nitroguanidinovaleric
acid),
the corresponding
2,4-dinitrophenylhydrazones,
and the flavianate of o(keto-&guanidinovaleric
acid is described.
The keto acids were slowly
reduced by lactic dehydrogenase, were not attacked by arginase, and underwent non-enzymatic
transamination
with pyridoxamine
at 100 to yield
arginine and nitroarginine,
respectively.
2. ar-Keto-6-N-carbobenzoxyvaleric
and a-keto+N-carbobenzoxycaproic
acids were prepared by enzymatic oxidation of the appropriate w-N-carbobenzoxy-L-amino
acids; the 2,4-dinitrophenylhydrazones
of these keto acids
are described.
3. The cr-keto analogues of lysine and ornithine were prepared from the
corresponding w-N-carbobenzoxyketo
acids by treatment with hydrobromic
acid in acetic acid solution.
The properties of the products obtained included ability to form 2,4-dinitrophenylhydrazones,
quantitative
decarboxylation
by ceric sulfate or hydrogen peroxide, and non-enzymatic
transamination
with pyridoxamine
to yield the corresponding amino acids.
After decarboxylation
with hydrogen peroxide, 6-aminovaleric
and y-aminobutyric
acids were formed, respectively,
from the cu-keto analogues
of lysine and ornithine.
4. Hydrogenation
of the or-keto analogues of lysine and ornithine, or
their w-N-carbobenzoxy
derivatives,
resulted in the formation of pipecolic
acid and proline, respectively,
a finding compatible with the expected
tendency to cyclization.
BIBLIOGRAPHY

1. Krebs,
H. A., Enzymologia,
2. Blanchard,
M., Green,
D.
421 (1944).

7, 53 (1939).
E., Nocito,
V.,

and

Ratner,

S., J.

Biol.

Chem.,

166,

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SUMMARY

il.

26.
27.
28.
29.

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MEISTER

THE -KETO ANALOGUES OF

ARGININE, ORNITHINE, AND LYSINE
Alton Meister
J. Biol. Chem. 1954, 206:577-585.

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