Amino Aldehydes

Catalog Product Name CAS Number Inquiry
BAT-000744 Boc-L-Valinal 79069-51-5 Inquiry
BAT-002696 Boc-NH-4,4-dimethylpentanal 892874-26-9 Inquiry
BAT-000399 Boc-L-alanine aldehyde 79069-50-4 Inquiry
BAT-000695 Boc-D-Phe-aldehyde 77119-85-8 Inquiry
BAT-000950 Boc-Phe-aldehyde 72155-45-4 Inquiry
BAT-000687 5-Benzyloxyindole-3-carboxaldehyde 6953-22-6 Inquiry
BAT-002695 Boc-NH-4-methyl-pentanal 644991-42-4 Inquiry
BAT-000688 5-Methylindole-3-carboxaldehyde 52562-50-2 Inquiry
BAT-002694 Indole-3-carboxaldehyde 487-89-8 Inquiry
BAT-000689 7-Methylindole-3-carboxaldehyde 4771-50-0 Inquiry
BAT-002697 5-Fluoroindole-3-carboxaldehyde 2338-71-8 Inquiry
BAT-009038 (9H-fluoren-9-yl)methyl 2-oxoethylcarbamate 156939-62-7 Inquiry
BAT-000747 Indole-4-carboxaldehyde 1074-86-8 Inquiry
BAT-008277 2-Amino-5-methylnicotinaldehyde 1023814-35-8 Inquiry
BAT-000696 Boc-D-Phg-aldehyde 137284-11-8 Inquiry
BAT-000704 Boc-NH-3-methylpent-4-enal 1335041-89-8 Inquiry
BAT-000742 Boc-Phg-aldehyde 163061-19-6 Inquiry
BAT-000743 Boc-Trp(Mts)-aldehyde 1026493-36-6 Inquiry
BAT-000690 Boc-beta-homoPhe(4-F)-aldehyde 1353876-38-6 Inquiry
BAT-000691 Boc-beta-Phe(4-F)-aldehyde 1353876-37-5 Inquiry

Introduction

Amino aldehydes are a group of compounds that have both amino (-NH2) and aldehyde (-CHO) groups. During the last decade α-amino aldehydes have attracted widespread attention as the important natural source of chiral substrates useful in stereocontrolled organic synthesis. They are of special interest due to their ready availability in both enantiomeric forms from natural sources, as well as their pronounced versatility, due to the presence of both the formyl group and suitably protected amino functionality in the molecule.

However, there is no possibility for intramolecular stabilization in the case of α-amino aldehydes. Owing to the presence of incompatible functional groups, this class of compounds is unstable. The history of α-amino aldehydes can be traced back to Fischer's discovery of glucosamine in 1902, in which unprotected amine and aldehyde functionalities are stabilized as a cyclic hemiacetal.

These bifunctional compounds exhibit a valuable dual reactivity, which has been utilized in a broad range of synthetic applications.

Applications

Medicine: Some peptide derivatives containing α-amino aldehyde unit are potent inhibitors of proteases, such as papain, thrombin, trypsin, calpain, caspases and viral proteases, which can be applied range from antiviral drugs to anti-thrombotic, anti-cataract or anti-tumor agents.

Intermediates: Aldehyde group can be transformed into a wide range of structural frameworks. Therefore, α-amino aldehydes are among the most widely used intermediates in synthesis.

Leading compounds: The amino aldehydes are not only potential drug candidates, but also useful precursors of other compounds, such as diamines, amino alcohols, etc. The development of new derivatives, especially those with α-substituted β-amino aldehyde residues, could be useful to discover new drug leads.

Building blocks: The juxtaposition of amino and aldehyde functionalities predisposes chiral amino aldehydes as divergent building blocks within organic chemistry.

References:

  1. Carlos J. Saavedra, Alicia Boto and Rosendo Hernández. Preparation of modified peptides: direct conversion of α-amino acids into β-amino aldehydes. Organic & Biomolecular Chemistry, 2012, 10(22): 4448-4461.
  2. Gryko D, Chalko J, Jurczak J. Synthesis and reactivity of N-protected-alpha-amino aldehydes. Chirality, 2003, 15(6): 514-541.
  3. Ryan Hili, Sivaraj Baktharaman, Andrei K Yudin. Synthesis of Chiral Amines Using α-Amino Aldehydes. European Journal of Organic Chemistry, 2008, 2008(31): 5201-5213.
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