Synthesis of a Puromycin Analog

Lichtenthaler, Frieder W.; Albrecht, Hans

doi:10.1002/anie.196804571

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1969

1979

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Cited by 6 publications

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“…1) Later this reaction was widely adopted for dialdehyde derived from aliphatic, aromatic compounds and nucleosides. [2][3][4][5][6][7] As examples of this reaction applied to polysaccharides cellulose 6 ) and starch 2 ) are enumerated. However, there is no clear conclusion about the constitution of the reaction products.…”

mentioning

confidence: 99%

Nitro- and Amino-polysaccharide Formation from Dextran

Maekawa

Miyoshi

Tsuru

1976

Agricultural and Biological Chemistry

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mentioning

confidence: 99%

Nitro- and Amino-polysaccharide Formation from Dextran

Maekawa

Miyoshi

Tsuru

1976

Agricultural and Biological Chemistry

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Nucleoside, V. 6‐Dimethylamino‐purin‐Nucleoside der 3‐Amino‐3‐desoxy‐β‐D‐glucose, ‐mannose und ‐galaktose

Lichtenthaler

Albrecht

1969

Chem. Ber.

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Nucleosides, XXXVI. Synthesis of 3′‐Homocitrullylamino‐ and 3′‐Lysylamino‐3′‐deoxyadenosine and Their Relation to Cordyceps militaris Derived Products

et al. 1979

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Syntheses of N6‐desmethylpuromycin (6), of 3′‐L‐homocitrullylamino‐3′‐deoxyadenosine (3) and its L‐lysyl analog 4 are reported, based on a preparatively efficient procedure for the preparation of 3′‐amino‐3′‐deoxyadenosine (2) from D‐xylose, and on attachment of the corresponding amino acid components via the N‐benzyloxycarbonyl‐blocked N ‐hydroxysuccinimidyl and p‐nitrophenyl derivatives Z,Z‐Lys‐OSU (18), Z‐Phe(OMe)‐OSU (20) and Z‐hCit‐ONP (23), each characterized in crystalline form. – Synthetic 3 was identical with the product isolated previously from Cordyceps militaris, thus now unequivocally establishing its structure. – In biological evaluation, 3 and 4 exhibited inhibition of poly (U) directed polyphenylalanine synthesis analogous to that of puromycin (5), yet lower by factors of 20 and 40, respectively, whilst that of 6 was identical with 5 qualitatively and quantitatively; hence, the N6‐methyl groups in 5 are not essential for termination of ribosomal peptide chain elongation.

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Synthesis of a Puromycin Analog

Cited by 6 publications

References 7 publications

Nitro- and Amino-polysaccharide Formation from Dextran

Nitro- and Amino-polysaccharide Formation from Dextran

Nucleoside, V. 6‐Dimethylamino‐purin‐Nucleoside der 3‐Amino‐3‐desoxy‐β‐D‐glucose, ‐mannose und ‐galaktose

Nucleosides, XXXVI. Synthesis of 3′‐Homocitrullylamino‐ and 3′‐Lysylamino‐3′‐deoxyadenosine and Their Relation to Cordyceps militaris Derived Products

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