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ChemFilesTitle Vol . 2, No. 4
Unnatural Amino Acids II
The latest Update on New Tools for Drug Discovery
Click here to download PDF version. (688 KB)

 

Introduction / Cyclic Amino Acids / Diamino Acids / ß-Amino Acids and Homo Amino Acids
Alanine Derivatives / Phenylalanine Boronic Acids / Proline and Pyroglutamine Derivatives
Other Amino Acid Building Blocks / Coupling Reagents / Preloaded Resins / Books

ß-Amino Acids and Homo Amino Acids

aminoacidIn the past few years ß-peptides and other ß-amino acid containing oligomers have emerged as very promising tools in medicinal chemistry, as they exhibit remarkable biological activity together with an extraordinary biological stability.1 ß-Peptides have shown to be stable to common peptidases for at least two days.2 Recently, a cyclic ß-tetrapeptide was synthesized with biological activity similar to somatostatine, an important endogenous neurotransmitter and inhibitor of hormone secretion.3 Systematic replacement of an ß-amino acid by an ß-amino acid residue resulted in a hybrid oligopeptide which binds to major histocompatibility complex (MHC) proteins, while showing enhanced stability towards proteolysis.4,5 Another important aspect of ß-peptide oligomers is their ability to fold into well defined and stable helical-, turn- and pleated sheet-conformations in solution.6-9 The picture aside shows a ß-peptide forming a two-stranded ß-pleated sheet connected by a hairpin turn. This sheet-and-turn structure was created and analysed by NMR in solution by Seebach and coworkers. It complements the similar structure described by Gelmann et al.10 by revealing the opposite orientation of the net dipole. Further remarkable applications of ß-amino acids are the use as protease inhibitors,11 precursors for antibiotics12 and building blocks in cryptophycins.13,14

New offerings in this rapidly expanding field are added monthly! When you cannot find the amino acid you are looking for, or for additional technical information, please contact your local Sigma-Aldrich Office.

 

Cat. No. Product Information Unit Sizes
03768 H-L-ß-Homopro-OH HCl (S)-2-(2-Pyrrolidinyl)acetic acid hydrochloride
>98.0% C6H11NO2•HCl Mr 129.16 [56633-75-1] structure 250mg; 1g
17988 H-DL-ß-Leu-OH (1)-3-Amino-4-methylpentanoic acid
>98.0% C6H13NO2 Mr 131.17 [5699-54-7] structure 1g; 5g
21625 H-DL-ß-Homoleu-OH (1)-3-Amino-5-methylcaproic acid
>99.0% C7H15NO2 Mr 145.20 [3653-34-7] structure 1g; 5g
71552 H-DL-ß-Phe-OH (1)-3-Amino-3-phenylpropionic acid
~99% C9H11NO2 Mr 165.19 [614-19-7] structure 1g; 5g
79995* L-Homophe-OEt HCl
>98.0% C12H17NO2•HCl Mr243.73 [90891-21-7] structure 10g; 100g
79995* L-Homophe-OEt HCl
>98.0% C12H17NO2•HCl Mr243.73 [90891-21-7] structure 10g; 100g
75854* D-Homophe-OEt HCl
>98.0% C12H17NO2•HCl Mr243.73 [90940-54-8]   10g; 100g
71044* N-Benzyl-L-Homophe-OEt HCl
>98.0% C19H23NO2•HCl Mr333.86   structure 10g; 100g
75664* N-Benzyl-D-Homophe-OEt HCl
>98.0% C19H23NO2•HCl Mr333.86   10g; 100g
41844 (1)-3-(Boc-amino)-4-(4-biphenylyl)butyric acid
>98.0% C21H25NO4 Mr355.43   structure 10g; 100g
23704 (1)-3-Amino-4-(4-biphenylyl)butyric acid hydrochloride
>98.0% C16H17NO2•HCl Mr291.78   250mg; 1g
70031* (+)-Ethyl (S)-2-amino-4-cyclohexylbutyrate hydrochloride
>98.0% C12H23NO2•HCl Mr 249.78   10g; 100g
78706* (-)-Ethyl (R)-2-amino-4-cyclohexylbutyrate hydrochloride
>98.0% C12H23NO2•HCl Mr 249.78     10g; 100g
68289 3-Amino-4,4,4-trifluorobutyric acid
>98.0% C4H6F3NO2 Mr157.09 [584-20-3]   500mg

* Produced by Ciba Specialty Chemicals Inc.

REFERENCES:

  1. Borman, S. Chem. Eng. News 1999, 77, 27.
  2. Seebach, D. Matthews, J. L. Chem Comm. 1997, 2015.
  3. Seebach D. et al., Angew. Chem. Int Ed. 1999, 38, 1223.
  4. Rognan, D. et. al., J. Med. Chem. 1999, 42, 2318.
  5. Rognan, D. et. al., J. Biol. Chem. 2001, 27, 24525.
  6. Seebach, D. et al., Angew. Chem. Int Ed. 1999, 38, 1595.
  7. Gademann, K. et al., Helv. Chim. Acta 1999, 82, 1.
  8. Gellman, S. H. et al., J. Am. Chem. Soc. 1999, 121, 6206.
  9. Gellman, S. H. et al., J. Am. Chem. Soc. 1999, 121, 7574.
  10. Gellman, S. H. et al., J. Am. Chem. Soc. 1998, 120, 10555.
  11. Takashiro et al., Bioorg. & Med. Chem. 1999, 7, 2063.
  12. Tymiak, A. A. et al., J. Org. Chem. 1989, 54, 1149.
  13. Eggen, M. et al., Org. Lett. 2001, 12, 1813.
  14. White, J. D. J. Org. Chem. 1999, 64, 6206.
   
 
 
 
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