Universal linker for combinatorial synthesis

Details Universal linker for combinatorial synthesis Universal linker for combinatorial synthesis

1998-03-16

1999-12-28

MacMillan, Keith D.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

436531, 436518, 436523, 530335, 562426, 562431, 562466, 562471, 562472, 564123, 564161, 564162, 564163, 568583, 568626, 568630, 568667, G01N 33543, G01N 33545, C07C 5948, C07C 5956, C07C23300

Patent

active

060083212

ABSTRACT:
A substrate for solid phase synthesis of the formula: ##STR1## is disclosed. Also disclosed are processes for preparing the substrate and intermediates useful therein. Among the novel intermediates are compounds of the formula: ##STR2## wherein t is 0 or 1; n is 3-20; R is OH, an activated ester or the residue of a solid support having a plurality of amino functionalities; A is --O-- or --NH-- and Q is hydrogen or a protecting group for an amine or alcohol.

REFERENCES:
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Florsheimer et al. "Solid-phase synthesis of peptides with the highly . . . " Peptides 131-133 (1990).
Sharma et al. "Reductive Amination with Tritylamine as an Ammonia Equivalent: . . . " J. Org. Chem. 58, 4993-4996 (1993).
Flechsler et al. "Anchor-linked Intermediates in Peptide Amide Synthesis are Caused . . . " J. Pept. Sci. 3, 191-200 (1995).
Seitz et al. "Chemoenzymatic Solution--and Solid-Phase Synthesis of . . . " J. Am. Chem. Soc. 119, 8766-8776 (1997).
Ngu et al. "Preparation of Acid--labile Resins with Halide Linkers and . . . " Tetrahedron Lett. 38, 973-976.
Raju et al. "Use of Halomethyl Resins to Immobilize Amines: An . . . " Tetrahedron Lett. 38, 4965-4968 (1977).
Backes et al. "Solid support linker strategies" Current Opinion in Chemical Biology 1, 86-93 (1997).
Chen et al. J. Amer. Chem. Soc., 1994, vol. 116, pp. 2661-2662, 1994.
Riniker, B. et al., "A General Strategy for the Synthesis of Large Peptides: The Combined Solid-Phase and Solution Approach," Tetrahedron, 49:9307-9320 (1993).

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