The ACTION OF PERIODIC ACID ON Α-Amino ALCOHOLS

Nicolet, Ben H.; Shinn, L. A.

doi:10.1021/ja01875a521

Cited by 164 publications

(51 citation statements)

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“…It is well known that the reaction leads to selective cleavage of the carbon-carbon bond of adjacent diols and converts them to dialdehyde groups without significant side reactions. In addition to the adjacent diols, other 1, 2-dioxygenated groups and 1, 2-aminoalcohols are also oxidatively cleaved by the periodate (Nicolet & Shinn, 1939). The adjacent diols which are substituted by etherifying agents including methyl, carboxymethyl and hydroxypropyl are prevented from cleavage by periodate ions (Edward Glass et al,1980;Vold & Christensen, 2005).…”

Section: Introductionmentioning

confidence: 99%

Selective oxidation and determination of the substitution pattern of hydroxypropyl guar gum

Chen

et al. 2010

Carbohydrate Polymers

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Section: Introductionmentioning

confidence: 99%

Selective oxidation and determination of the substitution pattern of hydroxypropyl guar gum

Chen

et al. 2010

Carbohydrate Polymers

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“…It has been reported (6)(7)(8) that the reaction between periodate and serine or threonine follows the scheme:…”

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confidence: 99%

The mechanism of the oxidative deamination and decarboxylation of serine and threonine by periodate in acid medium

Pascual¹,

Herraez²

1985

Can. J. Chem.

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ROSA PASCUAL and MIGUEL A. HERRAEZ. Can. J. Chem. 63, 2349 (1985). The kinetics of oxidation of serine and threonine by periodate have been investigated in acid medium at 10°C. The reaction rate is first order in both periodate and amino acid, and the overall reaction follows second-order kinetics. The rates decrease with increase in [H']. A catalytic effect of the buffers was not observed in the oxidation process. An analysis of the dependence of the rate on [H'] reveals that the reactive species under the experimental conditions are periodate monoanion and dianion and the dipolar form of the amino acid. The mechanism proposed and the derived rate law are consistent with the observed kinetics. The rate constants predicted using the derived rate law are in agreement with the observed rate constants, thus justifying this rate law and hence the proposed mechanistic scheme.ROSA PASCUAL et MIGUEL A. HERRAEZ. Can. J. Chem. 63, 2349 (1985). Operant h 10°C et dans un milieu acide, on a CtudiC la cinCtique de l'oxydation de la sCrine et de la thrkonine par le periodate. La rkaction est du premier ordre tant en periodate qu'en acide aminC et I'ensemble de la rkaction est du deuxibme ordre. Les vitesses diminuent avec une augmentation de I'aciditt. On n'a pas observk d'effet catalytique des tampons sur les processus d'oxydation. Une analyse de la relation entre les vitesses de rkaction et la concentration en H' rCvble que les espkces rCactives dans ces conditions expkrimentales sont les monoanion et dianion du periodate et la forme dipolaire de I'acide aminC. Le mCcanisme proposC ainsi que I'Cquation de vitesse qui en dCrive sont en accord avec les cinCtiques observCes. Les constantes de vitesse que I'on peut prCvoir en se basant sur I'Cquation de vitesse que I'on a obtenu sont en accord avec les constantes de vitesses observ6es et ces rksultats justifient cette Cquation de vitesse et donc le schCma mtcanistique proposC.[Traduit par le journal]

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“…Glucose, mannose or sialic acids are examples of possible pH 4-sensitive sites. An amino sugar (for example, glucosamine, or amino-terminal serine or threonine, which are known to be periodatesusceptible [19]) would be a logical candidate for a pH 7-susceptible site.…”

Section: Discussionmentioning

confidence: 99%

Inactivation of Mouse Elberfeld Virus by Periodate

Mak¹,

Rueckert²

1974

Intervirology

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Mouse Elberfeld virus (ME virus) is rapidly inactivated by sodium meta-periodate at millimolar concentrations. Inactivation was observed at all pH’s examined from 3 to 8, but showed two distinct optima, one at pH 4 and another at pH 7. Inactivation was accompanied at both pH’s by complete dissociation of the virion into its protein and RNA components. The infectivity of the RNA recovered from inactivated virions was the same as that of the untreated control. It is concluded that inactivation of viral infectivity is not due to attack on the RNA-genome but rather to attack by periodate on some component(s) of the viral capsid. The possible identity of the periodate-sensitive site is discussed.

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The ACTION OF PERIODIC ACID ON Α-Amino ALCOHOLS

Cited by 164 publications

References 0 publications

Selective oxidation and determination of the substitution pattern of hydroxypropyl guar gum

Selective oxidation and determination of the substitution pattern of hydroxypropyl guar gum

The mechanism of the oxidative deamination and decarboxylation of serine and threonine by periodate in acid medium

Inactivation of Mouse Elberfeld Virus by Periodate

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