Einfluß der syn-1,3-diaxialen wechselwirkung auf konformationsgleichgewichte der 2,4-diamino-2,4-didesoxy-α-d-idopyranose
1975; Elsevier BV; Volume: 45; Issue: 1 Linguagem: Inglês
10.1016/s0008-6215(00)85879-6
ISSN1873-426X
AutoresHans Paulsen, Hubert Koebernick,
Tópico(s)Amino Acid Enzymes and Metabolism
ResumoConformational equilibria of derivatives of 2,4-diamino-2,4-dideoxy-α-d-idopyranose are investigated. In the case of methyl 2,4-diacetamido-3,6-di-O-acetyl-2,4-dideoxy-α-d-idopyranoside, the proportion of the 1C4 conformation is between 7 and 44%, depending upon the solvent, and increases with increasing polarity of the solvent. Methyl 2,4-di(N-acetyl-N-acylamino)-3,6-di-O-acyl-2,4-dideoxy-α-d-idopyranosides show such strong steric 1,3-diaxial interaction that the proportion of the 1C4 conformation is 93%. Methyl 2,4-diamino-2,4-dideoxy-α-d-idopyranoside and its bis(ammonium) salt show strong 1,3-diaxial interactions of polar nature, resulting in an increase of the 1C4 conformation up to 74% and 84%, respectively. Conformational equilibria of derivatives of 2,4-diamino-2,4-dideoxy-α-d-idopyranose are investigated. In the case of methyl 2,4-diacetamido-3,6-di-O-acetyl-2,4-dideoxy-α-d-idopyranoside, the proportion of the 1C4 conformation is between 7 and 44%, depending upon the solvent, and increases with increasing polarity of the solvent. Methyl 2,4-di(N-acetyl-N-acylamino)-3,6-di-O-acyl-2,4-dideoxy-α-d-idopyranosides show such strong steric 1,3-diaxial interaction that the proportion of the 1C4 conformation is 93%. Methyl 2,4-diamino-2,4-dideoxy-α-d-idopyranoside and its bis(ammonium) salt show strong 1,3-diaxial interactions of polar nature, resulting in an increase of the 1C4 conformation up to 74% and 84%, respectively.
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