Zur Spezifität der α‐Glucosidase aus Hefe

Helferich, Burckhardt; Klein, Wilhelm; Schäfer, Wilhelm

doi:10.1002/cber.19260590110

Cited by 34 publications

(8 citation statements)

References 1 publication

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“…The l3C nmr spectra were obtained on Varían XL-100 (25 MHz) and (20 MHz) spectrometers in sample tubes of outside diameter 12 and 10 mm, respectively. nmr spectra were obtained on samples in tubes of 5 mm o.d.…”

Section: Methodsmentioning

confidence: 99%

Composition, sequence, and conformation of polymers and oligomers of glucose as revealed by carbon-13 nuclear magnetic resonance

Colson¹,

Jennings²,

Smith³

1974

J. Am. Chem. Soc.

268

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Section: Methodsmentioning

confidence: 99%

Composition, sequence, and conformation of polymers and oligomers of glucose as revealed by carbon-13 nuclear magnetic resonance

Colson¹,

Jennings²,

Smith³

1974

J. Am. Chem. Soc.

268

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“…Catalytic hydrogenolysis of 9a afforded lob but attempted C-6 selective benzoylation of this latter compound resulted in a complex mixture. Accordingly, a solution of lob and trityl chloride in anhydrous pyridine was allowed to stand at room temperature (19,20) until the reaction was complete (t.l.c. ), whereupon excess methanesulfonyl chloride was added to esterify the secondary hydroxyl groups leading to 100.…”

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confidence: 99%

The Synthesis of Some Alkyl Hex-3-enopyranosiduloses

Holder¹,

Fraser‐Reid²

1973

Can. J. Chem.

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Routes to methyl 3,4-dideoxy-a-D-glycero-hex-3-enopyranosidulose l a have been developed which use cheap readily-available chemicals, which are operable on a large scale and which have readily crystallizable materials as key intermediates (Scheme 4). Extensive use is made of reductive elimination of vicinal sulfonyloxy groups which is shown to operate equally well whether these groups on the pyranoside ring are in cis or tratls relationship. Contrary to other reported cases, it is found that the carbon-2 allylic hydroxyl goup is oxidized with manganese dioxide whether it is in pseudoaxial o r equatorial orientation.Differentes methodes utilisant des produits chimiques peu cohteux et facilement disponibles, pouvant facilement Ctre rentables a grande tchelle et irnpliquant des produits intermediaires facilement cristallisables, on CtC developptes afin d'obtenir le n~tthyl dideoxy-3,4 a-D-glycero hexeno-3 pyranosidulose l a (schema 4). Dans ces methodes, on a tres souvent utilist la reaction d'elimination rtductive des groupes sulfonyloxy vicinaux qui fonctionne bien, indtpendamment de la relation cis ou trans pouvant exister entre ces groupes sur l'anneau pyranosyde. Contrairement a ce qui a dtja tte rapporte dans d'autres cas. on a trouvt que le groupe hydroxyle allylique sur le carbone-2 est oxyde a I'aide du bioxyde d e manganese sans tenir compte de son orientation pseudoaxiale ou Cquatoriale.Can. .I. Chem., 51, 3357 (1973) [Traduit par le journal]

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“…Interestingly, one of the biggest challenges in the synthesis of the block 1 was the removal of trityle protective group from 9 . In general, trityle ethers are considered as extremely unstable in an acid medium . However, we did not succeed to remove it using known approaches, that is, by interaction with: a) concentrated acetic acid, b) montmorillonite K 10, c) 15% hydrochloric acid in acetone, as well as d) by using the system proposed above to deprotect the derivative 6 .…”

Section: Resultsmentioning

confidence: 94%

“…In general, trityle ethers are considered as extremely unstable in an acid medium . However, we did not succeed to remove it using known approaches, that is, by interaction with: a) concentrated acetic acid, b) montmorillonite K 10, c) 15% hydrochloric acid in acetone, as well as d) by using the system proposed above to deprotect the derivative 6 . Thus, the structure 9 should be considered as an exceptional case to perform the detritylation that is probably due to important steric effects.…”

Section: Resultsmentioning

confidence: 94%

“…In order to obtain 6 , the etherification of the resulting alcoholate was performed by classical Williamson reaction with allyl bromide at 60–65 °C. The removal of the trityle protective group was done by interaction of 6 with the mixture of AcOH–H 2 O–acetone (4:1:3), accordingly to general recommendations, followed by a chromatographic purification step. In the second approach, the product 2 was obtained by direct reaction of 4 with sodium by using 10 times molar excess of 4 at 60–65 °C for 15 h or at room temperature for 3 d, followed by the etherification with allyl bromide as described above for 6 .…”

Section: Resultsmentioning

confidence: 99%

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Convenient Synthesis of a Polyester‐co‐Polyether Block for Assembling Biocompatible Hyperbranched Macromolecules

Elkin

Hildgen

2013

Macro Chemistry & Physics

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Synthesis of a novel multifunctional block based on asymmetrically substituted pentaerythritol, succinic acid, and tetraethylene glycol is reported. The proposed reaction conditions allow selective preparation of the product in high overall yield. The block can be used in the assembly of biocompatible polyester-co -polyether (PEPE) hyperbranched macromolecules, which allows the product to be considered as a promising intermediate for the development of new biomedical dendrimers. As an example, the use of the "block by block" strategy is employed to obtain a second-generation dendron. It is shown that the approach is much more effi cient than the pathway of step-by-step grafting of separate molecular fragments.

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Zur Spezifität der α‐Glucosidase aus Hefe

Cited by 34 publications

References 1 publication

Composition, sequence, and conformation of polymers and oligomers of glucose as revealed by carbon-13 nuclear magnetic resonance

Composition, sequence, and conformation of polymers and oligomers of glucose as revealed by carbon-13 nuclear magnetic resonance

The Synthesis of Some Alkyl Hex-3-enopyranosiduloses

Convenient Synthesis of a Polyester‐co‐Polyether Block for Assembling Biocompatible Hyperbranched Macromolecules

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