Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1979-11-02
1981-10-27
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 12, 536 17R, C07H 1522
Patent
active
042974852
ABSTRACT:
Aminoglycosidic antibiotic comprising a 6-0-(3"-aminoglycosyl)-2-deoxystreptamine optionally having a 4-0-(aminogycosyl) group, such as kanamycins, gentamicins, sisomicin, forms reversible complex with zinc cations by association of the zinc cations with some pairs of aminohydroxyl groups in the aminoglycoside, and the zinc-complexed amino groups are blocked from acylation. Reaction of this zinc complex with an acylation reagent having an amino-blocking acyl group brings about acylation of the non-complexed amino groups to give an N-acylated zinc complex, namely a complex of zinc cation with an N-acylated aminoglycosidic antibiotic derivative. Removal of zinc cations from N-acylated zinc complex yields a partially N-acylated aminoglycosidic antibiotic where 1- and 3"-amino groups are unprotected but all other amino groups protected with acyl group. Further reaction of this partially N-acylated product with a certain alkanoic acid or N-formyl-imidazole results in preferential acylation of 3"-amino group without 1-amino group being acylated, affording a 1-N-unprotected and other N-fully-protected derivative of the aminoglycosidic antibiotic which is valuable to be 1-N-acylated with .alpha.-hydroxy-.omega.-aminoalkanoic acid for high-yield production of known semi-synthetic 1-N-(.alpha.-hydroxy-.omega.-aminoalkanoyl)-aminoglycosidic antibiotic.
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Jikihara Tomo
Takagi Yasushi
Tsuchiya Tsutomu
Umezawa Hamao
Umezawa Sumio
Brown Johnnie R.
Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
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