Methods for making a dolastatin, auristatin or related compounds comprising the steps of providing a universal dolastatin core of Formula (I) reacting the C-terminal carboxylic acid group with an amine (A) to form an amide bond and reacting the N-terminal amine with a carboxylic acid (CA) to form an amide bond, wherein the steps can be performed in either order. Also provided are an isolated salt of the universal dolastatin core for use in preparation of dolastatins, auristatins and related compounds. Also provided are a number of intermediates and process steps which are useful for the preparation of high purity dolastatin core and high purity dolastatin and auristatin compounds.

Methods for making a dolastatin, auristatin or related compounds comprising the steps of providing a universal dolastatin core of Formula (I) reacting the C-terminal carboxylic acid group with an amine (A) to form an amide bond and reacting the N-terminal amine with a carboxylic acid (CA) to form an amide bond, wherein the steps can be performed in either order. Also provided are an isolated salt of the universal dolastatin core for use in preparation of dolastatins, auristatins and related compounds. Also provided are a number of intermediates and process steps which are useful for the preparation of high purity dolastatin core and high purity dolastatin and auristatin compounds.

Compound are described comprising a perfluorinated group bonded to at least one terminal photoinitiator group with an organic linking group comprising at least one amide moiety. The compound typically comprises the (e.g. Michael addition) reaction product of i) a compound comprising an acryl group and a photoinitiator group; and ii) an amino functional perfluorinated compound. Also described is a composition comprising at least one free-radically polymerizable (e.g. fluorinated) monomer, oligomer, or combination thereof; and the described fluorinated photoinitiator compound and methods.

Compound are described comprising a perfluorinated group bonded to at least one terminal photoinitiator group with an organic linking group comprising at least one amide moiety. The compound typically comprises the (e.g. Michael addition) reaction product of i) a compound comprising an acryl group and a photoinitiator group; and ii) an amino functional perfluorinated compound. Also described is a composition comprising at least one free-radically polymerizable (e.g. fluorinated) monomer, oligomer, or combination thereof; and the described fluorinated photoinitiator compound and methods.

Described herein are compounds and compositions characterized, in certain embodiments, by conjugation of various groups, such as lipophilic groups, to an amino or amide group of an amino acid, a linear or cyclic peptide, a linear or cyclic polypeptide, or structural isomer thereof, to provide compounds of the present invention, collectively referred to herein as “APPLs”. Such APPLs are deemed useful for a variety of applications, such as, for example, improved nucleotide delivery. Exemplary APPLs include, but are not limited to, compounds of Formula (I), (II), (III), (IV), (V), and (VI), and salts thereof, as described herein:

##STR00001##

wherein m, n, p, R′, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.8, Z, W, Y, and Z are as defined herein.

Described herein are compounds and compositions characterized, in certain embodiments, by conjugation of various groups, such as lipophilic groups, to an amino or amide group of an amino acid, a linear or cyclic peptide, a linear or cyclic polypeptide, or structural isomer thereof, to provide compounds of the present invention, collectively referred to herein as “APPLs”. Such APPLs are deemed useful for a variety of applications, such as, for example, improved nucleotide delivery. Exemplary APPLs include, but are not limited to, compounds of Formula (I), (II), (III), (IV), (V), and (VI), and salts thereof, as described herein:

##STR00001##

wherein m, n, p, R′, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.8, Z, W, Y, and Z are as defined herein.

The present invention provides a catalyst containing a Brønsted acid as a novel means capable of producing an amide compound by highly stereoselectively and/or highly efficiently causing an amidation reaction in a variety of substrates having a carboxylic ester group and an amino group.

The present invention provides a catalyst containing a Brønsted acid as a novel means capable of producing an amide compound by highly stereoselectively and/or highly efficiently causing an amidation reaction in a variety of substrates having a carboxylic ester group and an amino group.

Disclosed herein are methods of preparing N.sup.6-((2-azidoethoxy)carbonyl)lysine, N.sup.6-((2-azidoethoxy)carbonyl)-L-lysine, and N.sup.6-((2-azidoethoxy)carbonyl)-D-lysine. Also disclosed herein are the compounds tert-butyl N.sup.2-(tert-butoxycarbonyl)-N.sup.6-((2-chloroethoxy)carbonyl)-L-lysinate and tert-butyl N.sup.6-((2-azidoethoxy)carbonyl)-N.sup.2-(tert-butoxycarbonyl)-L-lysinate, and uses thereof.

Disclosed herein are methods of preparing N.sup.6-((2-azidoethoxy)carbonyl)lysine, N.sup.6-((2-azidoethoxy)carbonyl)-L-lysine, and N.sup.6-((2-azidoethoxy)carbonyl)-D-lysine. Also disclosed herein are the compounds tert-butyl N.sup.2-(tert-butoxycarbonyl)-N.sup.6-((2-chloroethoxy)carbonyl)-L-lysinate and tert-butyl N.sup.6-((2-azidoethoxy)carbonyl)-N.sup.2-(tert-butoxycarbonyl)-L-lysinate, and uses thereof.