Constrained Polypeptide Binders via Multi-Point Covalent Linking

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Solution Overview

Problem

Existing methods for generating small molecule binders with high affinity and specificity are limited, particularly for biological targets, as they often rely on large biopolymer structures and struggle with conformational flexibility and proteolytic degradation, and current strategies for attaching connector compounds to polypeptides are labor-intensive and not suitable for genetically encoded phage libraries.

Innovation Solution

The development of a method that links a connector compound, such as tris-(bromomethyl)benzene, to a polypeptide via at least three covalent bonds, creating conformationally constrained polypeptide loops that can interact with targets, thereby enhancing binding affinity and specificity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If biological in vitro selection techniques are used to isolate binding ligands, then large biopolymeric structures such as antibodies can be isolated, but the method is not practicable for isolating small molecule drugs and suffers from conformational flexibility and proteolytic degradation

Engineering Contradiction:
Improvebinding affinityVSAvoidapplicability to small molecules
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The invention divides the polypeptide into multiple segments by introducing cysteine residues at specific positions, allowing each segment to be independently constrained by connector compounds. This segmentation enables the creation of structurally defined small molecule-like binders while maintaining the genetic encodability and selection capabilities of biological systems.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention creates composite structures by combining genetically encoded polypeptide segments with chemically synthesized connector compounds (such as tris-(bromomethyl)benzene). This composite approach integrates the advantages of both biological molecules (specificity, encodability) and chemical molecules (structural constraint, stability).

Inventive Principle:
Principle #40Composite materials

2Reliability

If connector compounds are attached to polypeptides using existing methods, then binding affinity can be improved, but the process is labor-intensive and not suitable for genetically encoded phage libraries

Engineering Contradiction:
Improvebinding affinityVSAvoidlibrary generation efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The invention enables self-service by incorporating reactive cysteine residues directly into the genetically encoded polypeptide sequence. The polypeptide itself provides the necessary functional groups (thiol groups of cysteine) that react with connector compounds, eliminating the need for separate modification steps and enabling automated library generation.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The invention changes the chemical parameters of the polypeptide by introducing cysteine residues at specific positions, which provides reactive thiol groups. This parameter change enables efficient conjugation with connector compounds under mild conditions, making the process suitable for high-throughput library generation from genetically encoded phage libraries.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This approach allows for the creation of polypeptides with multiple binding loops, increasing binding affinity and specificity, and enables the generation of large libraries of constrained peptides that can bind to targets through multiple interactions, overcoming limitations of previous methods.

Implementation Method 1

a connector compound attached to said polypeptide, wherein said connector compound is attached to said polypeptide by at least three covalent bonds

Methodology Applied
Scientific EffectCovalent bonding: Chemical Bonding

Data Source

PatentEP2474613B2Methods and compositions
Publication Date: 2022.02.16 BICYCLERD LTD
  • EP2474613B2 patent drawingFigure 1
  • EP2474613B2 patent drawingFigure 2A~2B
  • EP2474613B2 patent drawingFigure 3A~3C

AI summary

The invention relates to a complex comprising a phage particle, said phage particle comprising (i) a polypeptide; (ii) a nucleic acid encoding the polypeptide of (i); (iii) a connector compound attached to said polypeptide wherein said connector compound is attached to the polypeptide by at least three discrete covalent bonds. The invention also relates to libraries, and to methods for making complexes and to methods of screening using same.