US 6,605,590 B1 · Oligomers and oligomeric segments of alpha-hydroxy carboxylic acids and alpha-amino acids

Abstract

An enzymatic synthesis and composition of α-hydroxy carboxylic acid and α-amino acid or peptide co-oligomers is disclosed wherein a residue of the α-hydroxy carboxylic acid is linked to a residue of the α-amino acid or peptide by an amide linkage. Proteolytic enzyme papain catalyzes co-oligomerization of the α-hydroxy carboxylic acid and α-amino acid. The degree and distribution of oligomerization varies upon the type and concentrations of different reaction mixtures utilized and upon the length of allowed reaction time. The resultant oligomers may be provided to ruminants as bioavailable amino acid supplements that are resistant to degradation in the rumen.

Claims22

Dependent claims

A composition comprising

wherein
is the residue of an α-hydroxy acid analog of a naturally occurring α-amino acid, wherein
R1 is hydrogen, hydrocarbyl or substituted hydrocarbyl,
R2 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or is another hydroxy protecting group selected from the group consisting of tert-butyldimethylsilyl (TBS), tert-butyldiphenylsilyl (TBPS), triethylsilyl (TES), trimethylsilyl (TMS), and triisopropylsilyl (TIPS),
R3 is hydrogen, hydrocarbyl or substituted hydrocarbyl,
each AA is the residue of an α-amino acid selected from the group consisting of α-amino acids independently of any other α-amino acid residue, and
n is at least 2,
wherein said R2 substituted hydrocarbyl moieties are hydrocarbyl moieties that are comprised of one or more substituted atoms other than carbon, wherein the substituted atoms are selected from the group consisting of oxygen, silicon, phosphorus, boron, sulfur, and halogen atoms.

5 more elements

Dependencies are inferred from the claim text.

Oligomers and oligomeric segments of alpha-hydroxy carboxylic acids and alpha-amino acids

Life of this patent

Oligomers and oligomeric segments of alpha-hydroxy carboxylic acids and alpha-amino acids

Life of this patent

Abstract

Claims22