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US 6,787,612 B1Granted
Resin derivatization method and uses thereof
AssigneeDendreon Corporation
InventorsDaniel V. Siev, J. Edward Semple, Michael I. Weinhouse
Life of this patent
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Abstract
This invention provides a method for producing a derivatized resin useful in the arts of solid-phase peptide synthesis, combinatorial chemistry, and peptide or protein purification and separation. Methods for synthesizing the derivatized resin, the prototypical example of which is hydrazyl-carbonyl-amino methylated polystyrene, are provided by this invention disclosure.
Claims16
A method for production of a derivatized resin represented by formula (I):
- R4-NH—(C═X)—Y—Z—SS (I)
- wherein:
- R4 is —NH—R3, —NH2, —OH, or —O—R3, wherein R3 is a protecting group, provided that when R4 is —NH—R3 or —O—R3, then the protecting group is removed and replaced by —H in the final product (I);
- X is O, S, or NR7;
- R7 is H, alkyl, alkenyl, aryl, aralkyl, cycloalkyl, or heterocycle;
- Y is absent, —NH—, or —CH2;
- Z is absent or is a substituent selected from the group consisting of —NH—, —O—, —(C═O)—, —S—, SO2-, alkyl, alkenyl, aryl, aralkyl, cycloalkyl, heterocycle, provided that when Y is absent and X is O or S, Z does not comprise —(C═O)— immediately adjacent to —(C═X)—, and when Y is —NH— and Z comprises an —NH— or an —S—, at least one carbon atom separates Y and the —NH— or —S— of Z, wherein functional groups of Z are protected;
- SS is a solid support;
- wherein said derivatized resin represented by formula (I) is prepared by a process comprising the steps of:
- (i) reacting a starting material represented by formula (C)
- R1-(C═X)—Y—Z—SS, (C)
- wherein R1 is a leaving group;
- with a reactant of formula (D)
- R4-NH2 (D)
- to form derivatized resin (I) of formula R4-NH—(C═X)—Y—Z SS;
- and
- (ii) recovering the derivatized resin (I);
- wherein said material represented by formula (C) is prepared by a process comprising the step of:
- (iv) reacting a starting material of formula (A)
- R—Y—Z—SS, (A)
- wherein R is a leaving group,
- with a reactant of formula (B)
- R1-(C═X)—R2, (B)
- wherein R2 is a leaving group, same or different than R1, to form said starting material (C) represented by formula
- R1-(C═X)—Y—Z—SS. (C)
22 more elements
Dependencies are inferred from the claim text.