2-(Fmoc-amino)-3-azidobutanoic acid

2-(Fmoc-amino)-3-azidobutanoic acid

Published on 13/11/2012

Building Blocks for the synthesis of 2,3-diaminobutanoic acid containing peptides or for Click reactions.

Building Blocks for the synthesis of 2,3-diaminobutanoic acid containing peptides or for Click reactions.
 Fmoc-L-Cys(Phacm)-OH

The azido function in 2-amino-3-azidobutanoic acid can be used for different applications: 

  1. The azido group can be reduced to an amino function and herby serve as masked amino group. It is of particular use, if additional orthogonalities are needed. Azido is stable towards treatment with piperidine (Fmoc deprotection), Pd(0) (Alloc removal) and acidic treatmet (cleavage of Mtt, Trt or other acid sensitive groups). However, as it is a pseudohalogenide, care has to be taken during coupling steps, as HATU will cause high racemization. This can be avoided using collidine or other non-nucleophilic bases instead of DIPEA.
  2. Certainly 2-amino-3-azidobutanoic acid can be used for any type of click conjugation with any available alkynyl residue forming click conjugates of peptides or any other organic molecule.
  3. Chiral α,β-diamins and diamino acids have become an increasing targeted functional motif in organic synthesis owing to their ubiquity in natural products and medicinal agents. For example, it is found in biotin, penicillins, and antiinfluenza neuraminidase inhibitor Tamiflu. Chiral vicinal diamines and their metal complexes have been employed in stereoselective organic synthesis, in particular, as chiral auxiliaries and ligands in catalytic asymmetric synthesis.

Reference:

  • α,β-Diamino Acids: Biological Significance and Synthetic Approaches; Alma Viso, Roberto Fernández de la Pradilla, Ana García, and Aida Flores;Chemical Reviews 2005; 105(8): 3167-3196. DOI: 10.1021/cr0406561.
  • Update 1 of: α,β -Diamino Acids: Biological Significance and Synthetic Approaches; Alma Viso, Roberto Fernández de la Pradilla, Mariola Tortosa, Ana García, and Aida Flores; Chem. Rev. 2011; 111: PR1–PR42. DOI 10.1021/cr100127y.
  • Orthogonally Protected Cyclo-ß-tertapeptides as Solid-Supported Scaffolds for the Synthesis of Glycoclusters; Pasi Virta, Marika Karskela, Harri Lönnberg; J.Org.Chem 2006; 71: 1989-1999.
  • Stereocontrolled Route to Vicinal Diamines by [3.3] Sigmatropic Rearrangement of Allyl Cyanate: Asymmetric Synthesis of anti-(2R,3R)-and syn-(2R,3S)-2,3-Diaminobutanoic Acids; Yoshiyasu Ichikawa, Haruka Egawa, Takashi Ito, Minoru Isobe, Keiji Nakano, and Hiyoshizo Kotsuki;Org.Lett. 2006; 8(25): 5737-5740.
  • Efficient Synthesis of orthogonally protected ant-2,3-diamino acids; Stefania Capone, Annalisa Guaregna, Giovanni Palumbo, Silvana Pedatella;Tetrahedron 2005; 61: 6575-6579.


FAA2095 FAA2040	Fmoc-Abu(3-N3)-OH (2S,3S)