IP Library › Granted Patent US 9,562,023
Granted Patent B2
US 9,562,023 · App. 13/418,917 · Granted Feb 7, 2017

Dipeptide mimics, libraries combining two dipeptide mimics with a third group, and methods for production thereof

Inventor: Kevin Burgess (College Station, TX)
Assignee: Kevin Burgess
C07D249/04C07D241/08C07D271/10C07D273/00C07D401/04C07D401/12C07D401/14C07D403/12C07D403/14C07D405/14C07D413/12C40B40/04C40B50/08
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Quick Facts
Patent No.
US 9,562,023
App. No.
13/418,917
Granted
Feb 7, 2017
Kind
B2
Abstract

Monovalent compounds having moieties comprising at least one amino acid side chain are bound to a core molecule, which also comprises a nucleophilic moiety bound to said core molecule. Monovalent compounds also comprise a macrocyclic ring, a nucleophilic moiety, and a spacer group. Monovalent compounds may be combined into bivalent and trivalent compounds, some of which may have a labeling tag. Methods of production of bivalent compounds and contemplated uses thereof are disclosed.

Claims (412)

1. A dipeptide mimic having the structure:

wherein R0 is a fluorescein tag, a biotin tag or a polyether tag.

2. A protein mimic having the structure:

wherein R0 is a fluorescein tag, a biotin tag or a polyether tag.

3. A protein mimic having the structure:

wherein R0 is a fluorescein tag, a biotin tag or a polyether tag.

4. A dipeptide mimic to mimic proteins in a protein-protein interactions having the structure

wherein R0 is a fluorescein tag and wherein R1, R2 and R1′ and R2′ are selected from

(a) R1 is (CH 2 ) 4 NH 2 , R2 is CHCH 3 CH 2 CH 3 ;

(b) R1 is —(CH 2 ) 4 NH 2 , R2 is —H;

(c) R1 is —CH 2 CH 2 COOH, R2 is —CHCH 3 CH 2 CH 3 ;

(d) R1 is —CH 2 CH 2 OH, R2 is —H;

(e) R1 is —CH 2 CHCH 3 OH, R2 is —H;

(f) R1 is —CH 2 CH 2 OH, R2 is —CH(CH 3 ) 2 ;

(g) R1 is —(CH 2 ) 4 NH 2 , R2 is —CHCH 3 OH;

(h) R1 is —CH 2 CHCH 3 OH, R2 is —(CH 2 ) 4 NH 2 ;

(i) R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —CH 3 ;

(j) R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —CHCH 3 CH 2 CH 3 ;

(k) R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —H;

(l) R1 is —CH 2 CH 2 COOH, R2 is —(CH 2 ) 4 NH 2 ;

(m) R1 is —CH 2 CH 2 COOH, R2 is —CH 3 ;

(n) R1 is —CH 2 CH 2 COOH, R2 is

(o) R1 is —(CH 2 ) 4 CH 3 , R2 is —(CH 2 ) 4 NH 2 ;

(h″) R1

R2 is —CHCH 3 CH 2 CH 3 ;

(i″) R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —CHCH 3 CH 2 CH 3 ;

(j″) R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is

(k″) R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —(CH 2 ) 4 NH 2 ;

(l″) R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —CH 2 CH 2 COOH;

(m″) R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is

(n″) R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is

(o″) R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —(CH 2 ) 4 NH 2 ;

(p″) R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 CH 2 COOH;

(q″) R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is

(r″) R1 is —CHNH 2 CH 2 OH, R2 is

(s″) R1 is —CHNH 2 CH 2 OH, R2 is —(CH 2 ) 4 NH 2 ;

(t″) R1 is —CHNH 2 CH 2 OH, R2 is —CH 2 CH 2 COOH;

(u″) R1 is —CHNH 2 CH 2 OH, R2 is —CHCH 3 CH 2 CH 3 ;

(v″) R1 is

R2 is —CH 2 CH 2 COOH;

(w″) R1 is

R2 is

(l′″) R1 is —CH 2 NH 2 , R2 is —(CH 2 ) 4 NH 2 ;

(m′″) R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —(CH 2 ) 3 NHCNHNH 2 ;

(n′″) R1 is —CHNH 2 (CH 2 ) 4 NH 2 , R2 is —CH 2 CH 2 COOH;

(o′″) R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 CONH 2 ;

(p′″) R1 is —CHNH 2 CH 2 CONH 2 , R2 is —(CH 2 ) 4 NH 2 ;

(q′″) R1 is —CHNH 2 CH(CH 3 ) 2 , R2 is —CH 2 CONH 2 ;

(r′″) R1 is —CHNH 2 CH 2 CONH 2 , R2 is —CH 2 CONH 2 ;

(s′″) R1 is —(CH 2 ) 2 SCH 3 , R2 is —CH 2 CH 2 COOH;

(t′″) R1 is —CHNH 2 (CH 2 ) 4 NH 2 , R2 is —CHCH 3 OH;

(u′″) R1 is —CH 2 NH 2 , R2 is —CH 2 COOH;

(v′″) R1 is —CHNH 2 , CH(CH 3 ) 2 , R2 is —CH 2 OH;

(w′″) R1 is —CHNH 2 CH 2 CONH 2 , R2 is —CH 2 COOH;

(x′″) R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 COOH

(y′″) R1 is —CHNH 2 CH 2 OH, R2 is —CH 2 COOH

(z″) R1 is —C 6 H 6 C 2 HN 3 CHCOOHCHCH 3 CH 2 CH 3 , R2 is —CH 2 CH(CH 3 ) 2 ;

(a″″) R1 is −C 5 H 3 NC 2 HN 3 CH 2 COOH, R2 is —CH 2 CH 2 CONH 2 ; or

(b″″) R1 is −C 5 H 3 NC 2 HN 3 CHCOOHCH 2 CCONH 2 , R2 is —CH 2 CH 2 CONH 2 ; and

(a) R1′ is —(CH 2 ) 4 NH 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

(b) R1′ is —(CH 2 ) 4 NH 2 , R2′ is —H;

(c) R1′ is —CH 2 CH 2 COOH, R2′ is —CHCH 3 CH 2 CH 3 ;

(d) R1′ is —CH 2 CH 2 OH, R2′ is —H;

(e) R1′ is —CH 2 CHCH 3 OH, R2′ is —H;

(f) R1′ is —CH 2 CH 2 OH, R2′ is —CH(CH 3 ) 2 ;

(g) R1′ is —(CH 2 ) 4 NH 2 , R2′ is —CHCH 3 OH;

(h) R1′ is —CH 2 CHCH 3 OH, R2′ is —(CH 2 ) 4 NH 2 ;

(i) R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —CH 3 ;

(j) R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

(k) R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —H;

(l) R1′ is —CH 2 CH 2 COOH, R2′ is —(CH 2 ) 4 NH 2 ;

(m) R1′ is —CH 2 CH 2 COOH, R2′ is —CH 3 ;

(n) R1′ is —CH 2 CH 2 OH, R2′ is

(o) R1′ is —(CH 2 ) 4 CH 3 , R2′ is —(CH 2 ) 4 NH 2 ;

(h″) R1′

R2′ is —CHCH 3 CH 2 CH 3 ;

(i″) R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

(j″) R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is

(k″) R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —(CH 2 ) 4 NH 2 ;

(l″) R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —CH 2 CH 2 COOH;

(m″) R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is

(n″) R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is

(o″) R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —(CH 2 ) 4 NH 2 ;

(p″) R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CH 2 COOH;

(q″) R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is

(r″) R1′ is —CHNH 2 CH 2 OH, R2′ is

(s″) R1′ is —CHNH 2 CH 2 OH, R2′ is —(CH 2 ) 4 NH 2 ;

(t″) R1′ is —CHNH 2 CH 2 OH, R2′ is —CH 2 CH 2 COOH;

(u″) R1′ is —CHNH 2 CH 2 OH, R2′ is —CHCH 3 CH 2 CH 3 ;

(v″) R1′ is

R2′ is —CH 2 CH 2 COOH;

(w″) R1′

R2′ is

(l′″) R1′ is —CH 2 NH 2 , R2′ is —(CH 2 ) 4 NH 2 ;

(m′″) R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —(CH 2 ) 3 NHCNHNH 2 ;

(n′″) R1′ is —CHNH 2 (CH 2 ) 4 NH 2 , R2′ is —CH 2 CH 2 COOH;

(o′″) R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CONH 2 ;

(p′″) R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —(CH 2 ) 4 NH 2 ;

(q′″) R1′ is —CHNH 2 CH(CH 3 ) 2 , R2′ is —CH 2 CONH 2 ;

(r′″) R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —CH 2 CONH 2 ;

(s′″) R1′ is —CHNH 2 (CH 2 ) 2 SCH 3 , R2′ is —CH 2 CH 2 COOH;

(t′″) R1′ is —CHNH 2 (CH 2 ) 4 NH 2 , R2′ is —CHCH 3 OH;

(u′″) R1′ is —CH 2 NH 2 , R2′ is —CH 2 CH 2 COOH;

(v′″) R1′ is —CHNH 2 CH(CH 3 ) 2 , R2′ is —CH 2 OH;

(w′″) R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —CH 2 CH 2 COOH;

(x′″) R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CH 2 COOH; or

(y′″) R1′ is —CHNH 2 CH 2 OH, R2′ is —CH 2 COOH.

5. A dipeptide mimic to mimic proteins in a protein-protein interactions having the structure

wherein R0 is a biotin tag and wherein R1, R2 and R1′ and R2′ are selected from

R1 is —(CH 2 ) 4 NH 2 , R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —(CH 2 ) 4 NH 2 , R2 is —H;

R1 is —CH 2 CH 2 COOH, R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —CH 2 CH 2 OH, R2 is —H;

R1 is —CH 2 CHCH 3 OH, R2 is —H;

R1 is —CH 2 CH 2 OH, R2 is —CH(CH 3 ) 2 ;

R1 is —(CH 2 ) 4 NH 2 , R2 is —CHCH 3 OH;

R1 is —CH 2 CHCH 3 OH, R2 is —(CH 2 ) 4 NH 2 ;

R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —CH 3 ;

R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —H;

R1 is —CH 2 CH 2 COOH, R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CH 2 CH 2 COOH, R2 is —CH 3 ;

R1 is —CH 2 CH 2 COOH, R2 is

R1 is —(CH 2 ) 4 CH 3 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is

R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is

R1 is —CHNH 2 CH 2 OH, R2 is

R1 is —CHNH 2 CH 2 OH, R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CH 2 OH, R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CH 2 OH, R2 is —CHCH 3 CH 2 CH 3 ;

R1 is

R2 is —CH 2 CH 2 COOH;

R1 is

R2 is

R1 is —CH 2 NH 2 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —(CH 2 ) 3 NHCNHNH 2 ;

R1 is —CHNH 2 (CH 2 ) 4 NH 2 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 CONH 2 ;

R1 is —CHNH 2 CH 2 CONH 2 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CH(CH 3 ) 2 , R2 is —CH 2 CONH 2 ;

R1 is —CHNH 2 CH 2 CONH 2 , R2 is —CH 2 CONH 2 ;

R1 is —CHNH 2 (CH 2 ) 2 SCH 3 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 (CH 2 ) 4 NH 2 , R2 is —CHCH 3 OH;

R1 is —CH 2 NH 2 , R2 is —CH 2 COOH;

R1 is —CHNH 2 , CH(CH 3 ) 2 , R2 is —CH 2 OH;

R1 is —CHNH 2 CH 2 CONH 2 , R2 is —CH 2 COOH;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 COOH

R1 is —CHNH 2 CH 2 OH, R2 is —CH 2 COOH

R1 is —C 6 H 6 C 2 HN 3 CHCOOHCHCH 3 CH 2 CH 3 , R2 is —CH 2 CH(CH 3 ) 2 ;

R1 is −C 5 H 3 NC 2 HN 3 CH 2 COOH, R2 is —CH 2 CH 2 CONH 2 ; or

R1 is −C 5 H 3 NC 2 HN 3 CHCOOHCH 2 CCONH 2 , R2 is —CH 2 CH 2 CONH 2 ; and

R1′ is —(CH 2 ) 4 NH 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —(CH 2 ) 4 NH 2 , R2′ is —H;

R1′ is —CH 2 CH 2 COOH, R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —CH 2 CH 2 OH, R2′ is —H;

R1′ is —CH 2 CHCH 3 OH, R2′ is —H;

R1′ is —CH 2 CH 2 OH, R2′ is —CH(CH 3 ) 2 ;

R1′ is —(CH 2 ) 4 NH 2 , R2′ is —CHCH 3 OH;

R1′ is —CH 2 CHCH 3 OH, R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —CH 3 ;

R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —H;

R1′ is —CH 2 CH 2 COOH, R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CH 2 CH 2 COOH, R2′ is —CH 3 ;

R1′ is —CH 2 CH 2 OH, R2′ is

R1′ is —(CH 2 ) 4 CH 3 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′

R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is

R1′ is —CHNH 2 CH 2 OH, R2′ is

R1′ is —CHNH 2 CH 2 OH, R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CH 2 OH, R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CH 2 OH, R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is

R2′ is —CH 2 CH 2 COOH;

R1′

R2′ is

R1′ is —CH 2 NH 2 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —(CH 2 ) 3 NHCNHNH 2 ;

R1′ is —CHNH 2 (CH 2 ) 4 NH 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CONH 2 ;

R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CH(CH 3 ) 2 , R2′ is —CH 2 CONH 2 ;

R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —CH 2 CONH 2 ;

R1′ is —CHNH 2 (CH 2 ) 2 SCH 3 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 (CH 2 ) 4 NH 2 , R2′ is —CHCH 3 OH;

R1′ is —CH 2 NH 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CH(CH 3 ) 2 , R2′ is —CH 2 OH;

R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CH 2 COOH; or

R1′ is —CHNH 2 CH 2 OH, R2′ is —CH 2 COOH.

6. A dipeptide mimic to mimic proteins in a protein-protein interactions having the structure

wherein R0 is a polyether tag having the structure

and

wherein R1, R2 and R1′ and R2′ are selected from

R1 is —(CH 2 ) 4 NH 2 , R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —(CH 2 ) 4 NH 2 , R2 is —H;

R1 is —CH 2 CH 2 COOH, R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —CH 2 CH 2 OH, R2 is —H;

R1 is —CH 2 CHCH 3 OH, R2 is —H;

R1 is —CH 2 CH 2 OH, R2 is —CH(CH 3 ) 2 ;

R1 is —(CH 2 ) 4 NH 2 , R2 is —CHCH 3 OH;

R1 is —CH 2 CHCH 3 OH, R2 is —(CH 2 ) 4 NH 2 ;

R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —CH 3 ;

R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —H;

R1 is —CH 2 CH 2 COOH, R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CH 2 CH 2 COOH, R2 is —CH 3 ;

R1 is —CH 2 CH 2 COOH, R2 is

R1 is —(CH 2 ) 4 CH 3 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is

R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is

R1 is —CHNH 2 CH 2 OH, R2 is

R1 is —CHNH 2 CH 2 OH, R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CH 2 OH, R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CH 2 OH, R2 is —CHCH 3 CH 2 CH 3 ;

R1 is

R2 is —CH 2 CH 2 COOH;

R1 is

R2 is

R1 is —CH 2 NH 2 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —(CH 2 ) 3 NHCNHNH 2 ;

R1 is —CHNH 2 (CH 2 ) 4 NH 2 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 CONH 2 ;

R1 is —CHNH 2 CH 2 CONH 2 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CH(CH 3 ) 2 , R2 is —CH 2 CONH 2 ;

R1 is —CHNH 2 CH 2 CONH 2 , R2 is —CH 2 CONH 2 ;

R1 is —CHNH 2 (CH 2 ) 2 SCH 3 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 (CH 2 ) 4 NH 2 , R2 is —CHCH 3 OH;

R1 is —CH 2 NH 2 , R2 is —CH 2 COOH;

R1 is —CHNH 2 , CH(CH 3 ) 2 , R2 is —CH 2 OH;

R1 is —CHNH 2 CH 2 CONH 2 , R2 is —CH 2 COOH;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 COOH

R1 is —CHNH 2 CH 2 OH, R2 is —CH 2 COOH

R1 is —C 6 H 6 C 2 HN 3 CHCOOHCHCH 3 CH 2 CH 3 , R2 is —CH 2 CH(CH 3 ) 2 ;

R1 is −C 5 H 3 NC 2 HN 3 CH 2 COOH, R2 is —CH 2 CH 2 CONH 2 ; or

R1 is −C 5 H 3 N C 2 HN 3 CHCOOHCH 2 CCONH 2 , R2 is —CH 2 CH 2 CONH 2 ; and

R1′ is —(CH 2 ) 4 NH 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —(CH 2 ) 4 NH 2 , R2′ is —H;

R1′ is —CH 2 CH 2 COOH, R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —CH 2 CH 2 OH, R2′ is —H;

R1′ is —CH 2 CHCH 3 OH, R2′ is —H;

R1′ is —CH 2 CH 2 OH, R2′ is —CH(CH 3 ) 2 ;

R1′ is —(CH 2 ) 4 NH 2 , R2′ is —CHCH 3 OH;

R1′ is —CH 2 CHCH 3 OH, R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —CH 3 ;

R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —H;

R1′ is —CH 2 CH 2 COOH, R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CH 2 CH 2 COOH, R2′ is —CH 3 ;

R1′ is —CH 2 CH 2 OH, R2′ is

R1′ is —(CH 2 ) 4 CH 3 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′

R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is

R1′ is αCHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is

R1′ is —CHNH 2 CH 2 OH, R2′ is

R1′ is —CHNH 2 CH 2 OH, R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CH 2 OH, R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CH 2 OH, R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is

R2′ is —CH 2 CH 2 COOH;

R1′

R2′ is

R1′ is —CH 2 NH 2 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —(CH 2 ) 3 NHCNHNH 2 ;

R1′ is —CHNH 2 (CH 2 ) 4 NH 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CONH 2 ;

R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CH(CH 3 ) 2 , R2′ is —CH 2 CONH 2 ;

R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —CH 2 CONH 2 ;

R1′ is —CHNH 2 (CH 2 ) 2 SCH 3 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 (CH 2 ) 4 NH 2 , R2′ is —CHCH 3 OH;

R1′ is —CH 2 NH 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CH(CH 3 ) 2 , R2′ is —CH 2 OH;

R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CH 2 COOH; or

R1′ is —CHNH 2 CH 2 OH, R2′ is —CH 2 COOH.

7. A dipeptide mimic to mimic proteins in a protein-protein interactions having the structure

wherein R0 is a 1,2,3-triazole-functionalized polyether tag and wherein R1, R2 and R1′ and R2′ are selected from

R1 is —(CH 2 ) 4 NH 2 , R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —(CH 2 ) 4 NH 2 , R2 is —H;

R1 is —CH 2 CH 2 COOH, R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —CH 2 CH 2 OH, R2 is —H;

R1 is —CH 2 CHCH 3 OH, R2 is —H;

R1 is —CH 2 CH 2 OH, R2 is —CH(CH 3 ) 2 ;

R1 is —(CH 2 ) 4 NH 2 , R2 is —CHCH 3 OH;

R1 is —CH 2 CHCH 3 OH, R2 is —(CH 2 ) 4 NH 2 ;

R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —CH 3 ;

R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —(CH 2 ) 3 NHCNHNH 2 , R2 is —H;

R1 is —CH 2 CH 2 COOH, R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CH 2 CH 2 COOH, R2 is —CH 3 ;

R1 is —CH 2 CH 2 COOH, R2 is

R1 is —(CH 2 ) 4 CH 3 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is

R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —CHCH 3 CH 2 CH 3 ;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2 is

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is

R1 is —CHNH 2 CH 2 OH, R2 is

R1 is —CHNH 2 CH 2 OH, R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CH 2 OH, R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CH 2 OH, R2 is —CHCH 3 CH 2 CH 3 ;

R1 is

R2 is —CH 2 CH 2 COOH;

R1 is

R2 is

R1 is —CH 2 NH 2 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —(CH 2 ) 3 NHCNHNH 2 ;

R1 is —CHNH 2 (CH 2 ) 4 NH 2 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 CONH 2 ;

R1 is —CHNH 2 CH 2 CONH 2 , R2 is —(CH 2 ) 4 NH 2 ;

R1 is —CHNH 2 CH(CH 3 ) 2 , R2 is —CH 2 CONH 2 ;

R1 is —CHNH 2 CH 2 CONH 2 , R2 is —CH 2 CONH 2 ;

R1 is —CHNH 2 (CH 2 ) 2 SCH 3 , R2 is —CH 2 CH 2 COOH;

R1 is —CHNH 2 (CH 2 ) 4 NH 2 , R2 is —CHCH 3 OH;

R1 is —CH 2 NH 2 , R2 is —CH 2 COOH;

R1 is —CHNH 2 , CH(CH 3 ) 2 , R2 is —CH 2 OH;

R1 is —CHNH 2 CH 2 CONH 2 , R2 is —CH 2 COOH;

R1 is —CHNH 2 CHCH 3 CH 2 CH 3 , R2 is —CH 2 COOH

R1 is —CHNH 2 CH 2 OH, R2 is —CH 2 COOH

R1 is —C 6 H 6 C 2 HN 3 CHCOOHCHCH 3 CH 2 CH 3 , R2 is —CH 2 CH(CH 3 ) 2 ;

R1 is —C 5 H 3 NC 2 HN 3 CH 2 COOH, R2 is —CH 2 CH 2 CONH 2 ; or

R1 is —C 5 H 3 N C 2 HN 3 CHCOOHCH 2 CCONH 2 , R2 is —CH 2 CH 2 CONH 2 ; and

R1′ is —(CH 2 ) 4 NH 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —(CH 2 ) 4 NH 2 , R2′ is —H;

R1′ is —CH 2 CH 2 COOH, R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —CH 2 CH 2 OH, R2′ is —H;

R1′ is —CH 2 CHCH 3 OH, R2′ is —H;

R1′ is —CH 2 CH 2 OH, R2′ is —CH(CH 3 ) 2 ;

R1′ is —(CH 2 ) 4 NH 2 , R2′ is —CHCH 3 OH;

R1′ is —CH 2 CHCH 3 OH, R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —CH 3 ;

R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —(CH 2 ) 3 NHCNHNH 2 , R2′ is —H;

R1′ is —CH 2 CH 2 COOH, R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CH 2 CH 2 COOH, R2′ is —CH 3 ;

R1′ is CH 2 CH 2 OH, R2′ is

R1′ is —(CH 2 ) 4 CH 3 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′

R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CH 2 CH(CH 3 ) 2 , R2′ is

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is

R1′ is —CHNH 2 CH 2 OH, R2′ is

R1′ is —CHNH 2 CH 2 OH, R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CH 2 OH, R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CH 2 OH, R2′ is —CHCH 3 CH 2 CH 3 ;

R1′ is

R2′ is —CH 2 CH 2 COOH;

R1′

R2′ is

R1′ is —CH 2 NH 2 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —(CH 2 ) 3 NHCNHNH 2 ;

R1′ is —CHNH 2 (CH 2 ) 4 NH 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CONH 2 ;

R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —(CH 2 ) 4 NH 2 ;

R1′ is —CHNH 2 CH(CH 3 ) 2 , R2′ is —CH 2 CONH 2 ;

R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —CH 2 CONH 2 ;

R1′ is —CHNH 2 (CH 2 ) 2 SCH 3 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 (CH 2 ) 4 NH 2 , R2′ is —CHCH 3 OH;

R1′ is —CH 2 NH 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CH(CH 3 ) 2 , R2′ is —CH 2 OH;

R1′ is —CHNH 2 CH 2 CONH 2 , R2′ is —CH 2 CH 2 COOH;

R1′ is —CHNH 2 CHCH 3 CH 2 CH 3 , R2′ is —CH 2 CH 2 COOH; or

R1′ is —CHNH 2 CH 2 OH, R2′ is —CH 2 COOH.

Assignments (4)
MERGER Recorded May 3, 2018
From: STRIKE BIO, INC.
To: GRADALIS, INC.
Reel/Frame 045709/0406 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2015
From: GRADALIS, INC.
To: STRIKE BIO, INC.
Reel/Frame 035603/0731 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE'S ADDRESS PREVIOUSLY RECORDED ON REEL 028108 FRAME 0524. ASSIGNOR(S) HEREBY CONFIRMS THE THE CORRECT ADDRESS IS P.O. BOX 13861, COLLEGE STATION, TX 77841-3861. Recorded Jul 18, 2012
From: THE TEXAS A&M UNIVERSITY SYSTEM
To: BURGESS, KEVIN
Reel/Frame 028594/0519 →
RELEASE AGREEMENT Recorded Apr 25, 2012
From: THE TEXAS A&M UNIVERSITY SYSTEM
To: BURGESS, KEVIN
Reel/Frame 028108/0524 →
Continuity (3)
Continuation 12181168 · Jul 28, 2008
Provisional Application 60952149 · Jul 26, 2007
Related Publication 20120232268A1 · Sep 13, 2012