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Preparation of lysine based macromolecular highly branched homogeneous compound

  • US 4,360,646 A
  • Filed: 04/29/1981
  • Issued: 11/23/1982
  • Est. Priority Date: 04/06/1979
  • Status: Expired due to Fees
First Claim
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1. Process of producing a macromolecule which comprises:

  • (A) an initiation stage wherein at least one source unit(S) is combined with at least one lysine unit by;

    (1) blocking the two amino groups of lysine by conversion of each to a t-butyloxyurethane group;

    thus protecting these amino groups against reaction with the carboxyl group;

    (2) blocking the free carboxyl group of the obtained diurethane, N,N'"'"'-(di(t-butyloxycarbonyl) lysine, by conversion thereof to an inert N-substituted amide of said carboxyl group, inert toward amino groups;

    (3) liberating the two lysine amino groups by hydrolysis of the two urethane groups whereby the t-butyloxycarbonyl groups are removed and decomposed to t-butanol and carbon dioxide;

    thus freeing the two amino groups and obtaining a Compound I;

    (B) a first growth stage wherein two lysine units (M) are linked to the lysine unit of Compound I by;

    (1) blocking the two amino groups of the lysine unit in Compound I as in step (A) (1) above by conversion of each to a t-butyloxy urethane group;

    (2) forming a Compound (II) by converting the free carboxyl group of the N,N'"'"'-di(t-butyloxycarbonyl) lysine, obtained in step (B) (1) above, to a carboxyl derivative reactive with amino groups;

    (3) contacting the diamino-containing Compound (I), obtained in step (A)(3) above, with the reactive carboxyl derivative, Compound (II) of step (B)(2) above, to form the linkage --CONH-- and thereby link the lysine unit (M) of Compound I via its two amino groups to each of two diurethane lysine units (M) of Compound II via their carboxyl groups; and

    then liberating the four blocked amino groups by hydrolysis of the four urethane groups as in step (A)(3) above thereby forming Compound III;

    (C) as a third stage, repeating the steps, as in the preceding stage, of blocking the lysine amino groups;

    coverting the carboxyls of such blocked lysines to a reactive derivative Compound II; and

    linking four of these Compound II molecules via their reactive carboxyl derivative, to the four amino groups in each molecule of Compound III; and

    then liberating the eight amino groups of the four newly added lysine units to form Compound IV;

    (D) repeating at least once more, the set of growth steps of stage (C) above, thereby at each new stage increasing by a factor of essentially 2, the number of lysine units contained in the resulting macromolecule.

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