`
`AMERICAN
`JOURNAL
`Vol.
`22, No.
`1969,
`January,
`1,
`Printed in U.S.A.
`
`OF
`
`CLINICAL
`
`Nu-rRrrloN
`33-37
`
`pp.
`
`Methionine,
`Taurine
`
`Cystine,
`
`Cysteine,
`Interrelationships
`Human
`Plasma1’2
`
`and
`
`in
`
`\VALTER
`
`D.
`
`BLOCK,
`
`PH.D.,
`
`MARA
`
`E. MARKOVS,
`
`B.S.,
`
`AND
`
`BETTY
`
`F.
`
`STEELE,
`
`PH.D.
`
`et
`
`al. (3),3
`multivitamin
`The
`
`to
`
`given.
`
`only
`
`adjust
`
`was
`which
`between
`
`amino
`
`to
`
`given
`
`daily,
`
`along
`
`with
`
`a
`
`a
`
`allowed
`before
`of
`
`(as
`
`and
`
`after
`convert
`to
`S-carboxymethyl
`
`T HE
`
`amino
`
`ONLY
`
`mainte-
`adult
`acid
`or
`
`sulfur-containing
`EXOGENOUS
`for
`necessary
`the
`acid
`in
`equilibrium
`nitrogen
`of
`nance
`amino
`(1).
`The
`is methionine
`man
`the
`body,
`directly
`by
`be
`utilized
`may
`transulfura-
`of metabolic
`a
`series
`undergo
`tion
`reactions
`involving
`homocysteine,
`cysta-
`thionine,
`cysteine,
`cystine,
`and
`taurine.
`In
`present
`investigation,
`sponse
`test
`of
`free
`cysteine,
`cystine,
`taurine
`was
`human
`adults
`The
`of
`rate
`appearance
`the
`compound
`in
`the
`and
`the
`presence
`the
`amino
`
`the
`to
`
`loads
`and
`studied.
`of
`plasma
`other
`
`of
`
`re-
`
`the
`L-methioflifle,
`by
`healthy,
`amount
`and
`administered
`its
`effects
`acids
`
`on
`were
`
`observed.
`control.
`
`One
`ranging
`subjects;
`throughout
`they
`lived
`University
`
`Test
`
`loads
`
`of
`
`leucine
`
`served
`
`as
`
`a
`
`MATERIALS
`
`AND
`
`METHODS
`
`male
`
`and
`
`two
`
`female
`
`adults,
`healthy
`as
`served
`years,
`30
`constant
`remained
`the
`investigation,
`
`to
`
`During
`
`in
`
`from
`age
`22
`weights
`their
`the
`study.
`Clinical
`the
`in
`of Michigan
`
`Research
`
`Center
`
`of the
`
`Medical
`
`Center.
`
`3.6 g, was
`supplement.4
`to
`period
`3-day
`were
`subjects
`acid
`amino
`test
`the
`diet
`the
`A period
`3 days, during
`least
`at
`diet was fed, intervened
`the constant
`with
`the different
`the
`tests
`each
`of
`On
`the day
`the test,
`breakfast
`acids.
`of
`withheld, and
`blood
`was withdrawn
`from
`was
`the
`subject.
`Five
`grams
`of
`the
`cubital
`vein
`of
`the
`L-methionine,
`cysteine
`(as
`monohydro-
`free
`chloride), cystine
`dihydrochloride),
`the
`tau-
`of water
`100
`ml
`rifle,
`or
`leucine
`dissolved
`in
`16 g of a commercial
`beverage,5 were
`containing
`Blood
`1-, 2-,
`given
`orally.
`was
`withdrawn
`at
`and
`4-hr
`intervals.
`from
`The
`fresh blood
`hourly
`period
`of
`withdrawal
`iodoacetic
`acid,
`NaHCO3,
`enediaminetetraacetate
`(4),
`Brigham
`et
`al.
`the stable
`teine
`The
`plasma
`was
`and
`other
`method
`step
`
`each subject for each
`with
`was
`treated
`disodium
`ethyl-
`the
`method
`of
`the
`unstable
`cys-
`derivative.
`centrifugation
`acids
`by
`that
`
`separated
`
`analysis
`
`prepared
`for
`ninhydrin-reacting
`of Stein
`and Moore
`wherein
`cysteine
`is
`oxidized
`
`by
`
`of
`amino
`substances
`(5),
`except
`
`to
`
`cystine
`
`and
`the
`the
`
`Downloaded from https://academic.oup.com/ajcn/article-abstract/22/1/33/4732931 by barrettrabinow@gmail.com on 16 May 2020
`
`omitted.
`
`until
`
`et
`
`al.
`
`The
`
`extracts
`
`were
`
`stored
`
`analyzed
`(6), modified
`
`by
`
`the
`use
`
`to
`
`method
`the
`
`of
`accelerated
`
`at
`
`was
`-20 C
`Spackman
`system.
`
`RESULTS
`
`concentrations
`The
`cystathionine,
`cysteine,
`
`of
`
`free
`cystine,
`
`methionine,
`taurine,
`
`Prepared
`Ohio.
`Cleveland,
`Decavitamins,
`N.Y.
`5Tang,
`
`Co.,
`
`General
`
`by
`
`Nutritional
`
`Biochemicals
`
`Corp.,
`
`Roenig
`
`Division,
`
`Chas.
`
`Pfizer
`
`and
`
`Foods
`
`Corp.,
`
`White
`
`Plains,
`
`N.Y.
`
`The
`
`subjects
`
`were
`
`fed
`
`constant
`
`diet
`
`35 g of
`rest
`from
`
`protein
`a
`
`special
`
`low
`
`g from
`32.5
`protein,
`
`a
`daily;
`
`that
`milk
`yeast-
`
`(2), and
`
`lettuce.
`
`as
`
`butter,
`
`Foods
`
`canned
`
`low
`
`in
`
`fruit,
`
`to
`
`ensure
`
`an
`
`adequate
`
`mixture
`
`of
`
`Leverton
`
`such
`included
`The
`mineral
`
`contained
`and
`the
`leavened
`
`protein
`and
`calorie
`
`bread
`
`content,
`
`were
`jelly
`intake.
`
`1 From
`
`the
`
`Department
`
`of Dermatology,
`
`Medical
`
`School,
`School
`Ann
`
`and
`of
`Arbor,
`2 Supported
`Health
`Grant
`
`Department
`Public
`Health,
`Michigan.
`part
`in
`AM-06825-04.
`
`Health
`of
`University
`
`Development,
`of Michigan,
`
`by
`
`National
`
`Institutes
`
`of
`
`33
`
`Eton Ex. 1063
`1 of 5
`
`
`
`34
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`Block
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`et
`
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`Eton Ex. 1063
`2 of 5
`
`(cid:1)
`(cid:1)
`(cid:1)
`(cid:1)
`(cid:1)
`(cid:1)
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`
`
`Methionine,
`
`Cysteinc,
`
`Cystinc,
`
`and
`
`Taurinc
`
`in
`
`Plasma
`
`35
`
`TABLE
`
`II
`
`Concentrations
`
`of
`
`certain
`
`amino
`
`acids in human
`plasma
`mg/lOO
`
`tests,
`
`tolerance
`
`during
`
`taurine-
`
`and
`
`leucine-
`
`ml
`
`Amino
`
`acid
`
`Taurine5
`
`Leucinea
`
`0 hr
`
`1 hr
`
`2 hr
`
`4 hr
`
`0 hr
`
`1 hr
`
`2 hr
`
`4 hr
`
`Methionine
`Cystathio-
`nine
`Cysteine
`
`Cystine
`
`0.15
`0.05
`
`0.17
`1.12
`
`±
`
`±
`
`±
`±
`
`0.02b
`0.00
`
`0.04
`0.39
`
`±
`
`0.10
`
`0.14
`>0.00
`
`±
`
`0.06
`
`0.19
`0.10”
`
`0.17
`>0.00
`
`±
`
`0.02
`
`023”
`0.08
`
`0.16
`0.02
`
`0.16
`0.11
`
`ned
`
`0.14
`0.10
`
`ncd
`
`0.28
`0.98
`19.54
`0.35
`
`1.37
`0.42
`
`±
`±
`
`0.23
`0.17
`
`1.56
`
`±
`
`0.21
`
`1.63
`
`±
`±
`±
`±
`
`±
`
`0.18
`0.22
`
`7.11
`0.02
`
`0.33”
`0.92
`
`14.78
`0.29
`
`0.20
`
`1.49
`
`±
`
`±
`±
`
`±
`
`0.20c
`0.89
`
`6.55
`0.38
`
`0.14
`
`8.03
`0.04
`
`0.20
`
`1.43
`
`±
`
`±
`±
`
`±
`
`0.36
`1.04
`1.66
`0.26
`
`0.23
`0.93
`1.36
`0.28
`
`0.17
`
`3.35
`0.12
`
`0.93
`1.36
`0.36
`
`0.86
`1.21
`0.34
`
`0.15
`
`1.23
`
`1.08
`
`1.00
`
`1.02
`
`Taurine
`
`Methionine
`
`sulfoxides
`
`Threonine
`
`fasting
`
`was
`
`withdrawn,
`
`5 g of
`
`free
`
`taurine
`
`or
`
`free
`
`L-leuCine
`
`in
`
`100
`
`ml
`
`of
`
`a
`
`Downloaded from https://academic.oup.com/ajcn/article-abstract/22/1/33/4732931 by barrettrabinow@gmail.com on 16 May 2020
`
`interrelationships
`the
`metabolites
`of
`human
`adults
`levels
`in
`plasma
`selected
`
`studying
`for
`the
`of
`some
`healthy
`intact
`metabolites’
`at
`blood
`withdrawn
`test
`doses
`of methionine,
`and
`taurine
`have
`general,
`metabolic
`by Meister
`
`the
`
`(7).
`
`been
`
`methionine
`may
`derived
`intervals
`cysteine,
`administered.
`pathway
`
`be
`
`in
`the
`from
`after
`cystine,
`
`In
`
`outlined
`
`Met
`
`-,
`
`Cystathionine
`
`s-i
`
`Cys
`
`s-i
`Ser
`
`Cyst
`J.
`Taurinc
`
`operative
`
`appeared
`this
`study.
`The
`relationship
`cysteine,
`and
`cystine
`ticularly
`intriguing.
`ingested,
`cysteine
`absolute
`amount,
`
`under
`
`the
`
`conditions
`
`of
`
`among
`the
`in
`When
`values,
`tended
`
`free methionine,
`plasma
`was
`methionine
`although
`to
`follow
`
`lower
`the
`
`par-
`was
`in
`
`same
`
`plasma
`during
`and
`occurred
`
`ele-
`were
`4 hr
`the
`cystine-
`during
`
`tests.
`and
`acids
`determined
`glutamic
`isoleucine,
`
`ninhy-
`(as-
`acid,
`leu-
`
`of
`level
`cysteine-,
`increase
`No
`leucine
`amino
`free
`substances
`glutamine,
`valine,
`
`in
`increase
`regardless
`acids
`was
`increase
`when
`effect
`
`cystine
`amino
`sustained
`centration
`the
`lack
`
`of
`
`plasma
`of
`ingested;
`in
`taurine
`of
`
`levels
`which
`
`3)
`
`plasma
`was
`leucine
`
`of
`of
`the
`
`cysteine
`these
`rapid
`
`taurine
`given;
`ingestion
`
`and
`
`or
`two
`and
`
`con-
`4)
`on
`
`any
`acids
`
`of
`
`the
`and
`
`free
`other
`compounds
`
`S-containing
`determined
`
`amino
`
`in
`
`contents
`fasting
`
`Plasma.
`ilireonine
`the
`vated
`over
`the
`of
`methionine-,
`tolerance
`tests.
`the
`taurine
`and
`The
`other
`drin-reacting
`paragine
`citrulline,
`
`plus
`glycine,
`
`After
`
`the
`
`blood
`
`commercial
`jects.
`
`beverage
`c Average
`
`(Tang,
`value
`
`for
`
`General
`two
`
`Foods)
`subjects.
`
`were
`d Not
`
`to
`given
`calculated
`
`each
`
`subject.
`for
`technical
`
`dissolved
`±
`
`b Mean
`reasons.
`
`SD
`
`for
`
`three
`
`sub-
`
`sulfoxides,
`the
`
`metliioni iie
`plasma
`during
`and
`cystine-tolerance
`taurine
`and
`leucine
`II, respectively.
`I and
`The
`salient
`results
`tests
`appeared
`to
`be:
`
`tests
`
`and
`methionine-,
`tests,
`and
`are
`given
`
`threonine
`cysteine-,
`during
`in Tables
`
`in
`
`the
`
`from
`1)
`
`tolerance
`the
`concomitant
`
`the
`
`tyrosine,
`
`cine,
`histidine,
`casionally
`in
`general
`amount
`were
`
`phenylalanine,
`in
`arginine)
`and
`transitory
`a
`showed
`either
`were
`they
`that
`the
`below
`not affected.
`
`sen
`
`lysine,
`the
`plasma
`increase,
`decreased
`fasting
`level
`
`ne,
`oc-
`but
`in
`or
`
`of
`
`in
`
`concentration
`
`cysteine
`
`and
`methionine
`remained
`
`in
`
`the
`while
`test,
`essentially
`
`between
`plasma
`cystine
`the
`
`methio-
`during
`concen-
`same;
`
`2)
`
`increase
`nine
`the
`tration
`
`the
`
`COMMENTS
`
`The
`appear
`
`of
`
`results
`to
`indicate
`
`the
`
`present
`one
`
`that
`
`investigation
`the
`indices
`
`of
`
`among
`
`Eton Ex. 1063
`3 of 5
`
`
`
`to
`
`Block
`
`et
`
`a!.
`
`36
`
`general
`throughout
`amounts
`constant.
`test
`amino
`free
`cysteine
`
`cysteine
`tant
`
`The
`tionship
`that
`of
`not
`
`was
`increase
`reason
`in
`supposedly
`the
`same
`known,
`the
`
`trend
`
`of
`In
`
`those
`as
`tolerance
`the
`cystine
`free
`contrast,
`acid,
`a
`in
`the
`
`of
`period,
`remained
`when
`cystine
`concomitant
`plasma
`
`methionine
`while
`relatively
`was
`increase
`occurred;
`
`the
`
`the
`in
`
`when
`
`there
`ingested
`cystine.
`in
`free
`this
`for
`plasma
`arise
`amino
`and
`
`the
`
`one
`
`was
`
`a
`
`concomi-
`
`difference
`among
`from
`acid,
`may
`
`in
`
`rela-
`acids
`
`amino
`transulfuration
`methionine,
`only
`speculate
`
`is
`
`as
`
`to
`
`cause.
`
`That
`excess
`
`to
`
`differences
`the
`excretion
`
`of
`
`one
`
`probably
`or more
`
`are
`of
`
`due
`these
`
`g
`
`because
`21.0
`
`after
`
`would
`
`acids
`amino
`urine
`24-hr
`of methionine
`cysteine
`after
`2.4 mg
`cystine
`plus
`g of
`cystine;
`9.8
`mg
`test
`load
`
`of
`7.3
`and
`a
`
`of
`of
`
`seem
`samples
`11.9
`and
`load
`test
`a
`of methionine
`after
`cysteine
`and
`2.4 mg
`of
`cystine
`plus
`7.3
`g
`cys-
`
`un-
`con-
`mg
`of
`
`of
`
`is
`
`of
`
`or
`
`alterations
`due
`amino
`cellular
`the
`difference
`human
`adults
`taming
`amino
`levels
`the
`seem
`The
`after
`tion
`reduced
`been
`That
`concentration
`thionine-tolerance
`been
`shown
`laboratory;
`threonine
`from
`threefold
`ples
`(8).
`
`in
`worthy
`increase
`cysteine
`suggests
`form
`previously
`the
`
`bloods
`that
`
`plasma
`inges-
`the
`has
`
`me-
`has
`this
`
`was
`sam-
`
`tau-
`in
`
`from
`as
`(7).
`threonine
`the
`artifact
`from
`apparent
`obtained
`
`was
`
`during
`an
`studies
`
`the
`
`studies
`of
`plasma
`with
`iodoacetate
`untreated
`control
`
`SUMMARY
`
`cysteine-,
`studies
`adult
`
`cystine-,
`carried
`to
`
`and
`the
`
`extra-
`reason,
`healthy
`S-con-
`their
`
`to
`
`by
`enough
`
`intra-
`between
`acids.
`Whatever
`response
`by
`in
`test
`to
`acids
`plasma
`of
`further
`in
`
`intact
`of
`these
`doses
`as measured
`is
`striking
`investigation.
`taurine
`after
`
`in
`free
`cystine
`not
`but
`arises
`taurine
`that
`acid,
`the
`amino
`of
`indicated
`by Meister
`apparent
`increase
`in
`of
`plasma
`test
`previous
`in
`those
`in
`contents
`treated
`of
`the
`
`Downloaded from https://academic.oup.com/ajcn/article-abstract/22/1/33/4732931 by barrettrabinow@gmail.com on 16 May 2020
`
`a
`
`and
`out
`were
`investigate
`subjects
`human
`these
`S-con-
`among
`interrelationships
`plasma.
`A con-
`the
`in
`compounds
`in methionine
`and
`cys-
`increase
`during
`the
`methionine
`found
`concentrations
`remained
`cystine
`when
`contrast,
`was
`acid,
`increased
`of
`in
`the
`ingested,
`cystine
`in
`sustained
`and
`concentration
`test.
`
`the
`cys-
`when
`in-
`
`was
`
`tail-
`
`the
`no
`
`Methionine-,
`rine-tolerance
`healthy
`the
`taining
`comitant
`was
`teine
`while
`test,
`constant.
`test
`amino
`teine
`appeared
`
`In
`
`cysteine
`
`was
`
`crease
`rapid
`rifle
`erance
`S-containing
`effect
`on
`acids
`in
`
`Ingestion
`amino
`amounts
`
`the
`plasma.
`
`occurred.
`increase
`during
`of
`acids
`
`of
`
`cystine
`amounts
`and
`plasma;
`a
`concomitant
`There
`in
`plasma
`the
`taurine-tol-
`test
`loads
`of
`had
`little
`or
`the
`other
`amino
`
`REFERENCES
`
`acid
`
`of
`
`W.
`The
`C.
`1. RosE,
`requirements
`amino
`27:
`631,
`1957.
`man.
`adult
`Rev.
`Abstr.
`Nutr.
`B. F., M. C. HJ#{246}RTLAND AND W. D. BLOCK.
`2. STEELE,
`A yeast-leavened,
`low-protein
`bread
`for
`research
`diets.
`405,
`1965.
`J. Am.
`Assoc.
`
`Dietet.
`
`47:
`
`S-containing
`likely
`tained
`mg
`plus
`of
`cystine
`9
`of methionine;
`24.2
`mg
`and
`load
`of
`test
`a
`methionine
`cysteine
`teine.
`Perhaps
`with
`a
`cystine,
`taneous
`cystine,
`
`large
`there
`conversion
`or
`of
`cystine
`
`adult
`when
`amount
`is
`a
`
`man
`either
`and
`absorbed
`cysteine.
`
`to
`
`confronted
`cysteine
`almost
`cysteine
`But
`
`simul-
`
`to
`
`when
`
`rapid
`of
`
`able
`by
`this
`absorbed
`other
`noted
`
`ingested,
`is
`cope
`to
`transulfuration
`may
`be
`rapidly
`
`with
`
`metabolic
`added
`form
`
`the
`the
`to
`changed
`
`to
`
`sys-
`
`methio-
`cysteine
`cystine
`
`by
`metabolic
`in
`the
`
`the
`
`body
`functions.
`elevation
`
`after
`some
`hand,
`
`the
`
`ingestion
`to
`credence
`the
`differences
`
`tissues
`
`or
`
`enter
`rapid-
`
`The
`cysteine
`
`methionine
`theory.
`in
`amounts
`
`in
`
`On
`
`of
`
`of
`this
`
`cystine
`and
`of methionine,
`be
`indicative
`
`in
`
`plasma
`or
`
`the
`cysteine,
`of
`metabolic
`
`after
`cystine
`con-
`
`version,
`among
`intestinal
`
`but
`may
`S-containing
`or
`renal
`
`reflect
`
`interrelationships
`acids
`sites,
`
`amino
`absorption
`
`at
`or
`
`the
`be
`
`methionine
`tem
`is
`nine
`and
`and
`into
`ity
`plasma
`
`may
`
`the
`
`lend
`other
`
`cysteine
`of
`ingestion
`may
`
`not
`
`Eton Ex. 1063
`4 of 5
`
`
`
`Methionine,
`
`Cysteine,
`
`Cystine,
`
`and
`
`Taurine
`
`in
`
`Plasma
`
`37
`
`6.
`
`D. H., W. H.
`STEIN
`recording
`apparatus
`amino
`acids.
`
`of
`
`AND
`for
`Anal.
`
`S. Mooit(cid:1).
`use
`in
`the
`30:
`Chem.
`
`Downloaded from https://academic.oup.com/ajcn/article-abstract/22/1/33/4732931 by barrettrabinow@gmail.com on 16 May 2020
`
`Acids.
`
`STEELE.
`
`on
`
`the
`Proc.
`
`3. LEVERTON,
`E.
`BR000VSKY
`tive
`amino
`I. Threoninc.
`
`4.
`
`R. GRAM, M.
`R. M., M.
`A. MITCHELL.
`The
`AND
`of
`requirements
`young
`acid
`1956.
`59,
`58:
`J. Nutr.
`The
`AND S. MooltE.
`M. P., W. H.
`STEIN
`BRIGHAM,
`human
`cystine
`in
`and
`of
`cysteine
`concentrations
`39:
`1683,
`Invest.
`J. Clin.
`1960.
`blood
`plasma.
`Free
`amino
`acids
`H., AND S. Moos.x.
`5. STEIN,
`W.
`blood
`211:
`J.
`Biol.
`Chem.
`human
`plasma.
`1954.
`
`CHALOUPKA,
`quantita-
`women.
`
`of
`915,
`
`SPACKMAN,
`Automatic
`chromatography
`1190,
`1958.
`A.
`7. MEISTER,
`the
`of
`Biochemistry
`757-818.
`1965,
`Academic,
`York:
`New
`8. BLOCK, W. D., M. E. MARKOV5
`AND B. F.
`addition
`Effect
`of
`iodoacetate
`to
`blood
`of
`concentration
`free
`amino
`acids.
`731,
`1968.
`Soc.
`Exptl.
`
`Amino
`
`plasma
`Med.
`
`128:
`
`Biol.
`
`Eton Ex. 1063
`5 of 5
`
`