Need Assistance?

  • US & Canada:
    +
  • UK: +
Amino Aldehydes

Boc-NH-TMBheptyl-CHO

CAS 1353876-19-3
Catalog BAT-000739
Molecular Weight 281.39
Molecular Formula C16H27NO3
Boc-NH-TMBheptyl-CHO

Boc-NH-trans-cyclohexane-CHO

CAS 956325-28-3
Catalog BAT-000740
Molecular Weight 227.3
Molecular Formula C12H21NO3
Boc-NH-trans-cyclohexane-CHO

Boc-NH-trans-cyclopentane-CHO

CAS 1353093-76-1
Catalog BAT-000741
Molecular Weight 213.27
Molecular Formula C11H19NO3
Boc-NH-trans-cyclopentane-CHO

Boc-Phg-aldehyde

CAS 163061-19-6
Catalog BAT-000742
Molecular Weight 235.28
Molecular Formula C13H17NO3
Boc-Phg-aldehyde

Boc-Trp(Mts)-aldehyde

CAS 1026493-36-6
Catalog BAT-000743
Molecular Weight 470.58
Molecular Formula C25H30N2O5S
Boc-Trp(Mts)-aldehyde

Boc-L-Valinal

CAS 79069-51-5
Catalog BAT-000744
Molecular Weight 201.26
Molecular Formula C10H19NO3
Boc-L-Valinal

Fmoc-NH-hex-5-enal

Catalog BAT-000745
Molecular Weight 335.4
Molecular Formula C21H21NO3
Fmoc-NH-hex-5-enal

Fmoc-NH-pent-4-enal

CAS 1824023-93-9
Catalog BAT-000746
Molecular Weight 321.4
Molecular Formula C20H19NO3
Fmoc-NH-pent-4-enal

Indole-4-carboxaldehyde

CAS 1074-86-8
Catalog BAT-000747
Molecular Weight 145.16
Molecular Formula C9H7NO
Indole-4-carboxaldehyde

Ac-Phg(4-OH)-OEt

CAS 117785-07-6
Catalog BAT-000781
Molecular Weight 237.25
Molecular Formula C12H15NO4
Ac-Phg(4-OH)-OEt

Boc-Phe-aldehyde

CAS 72155-45-4
Catalog BAT-000950
Molecular Weight 249.31
Molecular Formula C14H19NO3
Boc-Phe-aldehyde

Indole-3-carboxaldehyde

CAS 487-89-8
Catalog BAT-002694
Molecular Weight 145.16
Molecular Formula C9H7NO
Indole-3-carboxaldehyde

Boc-NH-4-methyl-pentanal

CAS 644991-42-4
Catalog BAT-002695
Molecular Weight 215.29
Molecular Formula C11H21NO3
Boc-NH-4-methyl-pentanal

Boc-NH-4,4-dimethylpentanal

CAS 892874-26-9
Catalog BAT-002696
Molecular Weight 229.32
Molecular Formula C12H23NO3
Boc-NH-4,4-dimethylpentanal

5-Fluoroindole-3-carboxaldehyde

CAS 2338-71-8
Catalog BAT-002697
Molecular Weight 163.15
Molecular Formula C9H6FNO
5-Fluoroindole-3-carboxaldehyde

2-Amino-5-methylnicotinaldehyde

CAS 1023814-35-8
Catalog BAT-008277
Molecular Weight 136.15
Molecular Formula C7H8N2O
2-Amino-5-methylnicotinaldehyde

2-Fluoro-3-formylpyridine-4-boronic acid pinacol ester

CAS 1310384-06-5
Catalog BAT-008282
Molecular Weight 251.06
Molecular Formula C12H15BFNO3
2-Fluoro-3-formylpyridine-4-boronic acid pinacol ester

5-Bromofuro(2,3-b)pyridine-2-carbaldehyde

CAS 1299607-73-0
Catalog BAT-008300
Molecular Weight 226.03
Molecular Formula C8H4BrNO2
5-Bromofuro(2,3-b)pyridine-2-carbaldehyde

6-Chloro-3-methylpicolinaldehyde

CAS 1211537-07-3
Catalog BAT-008314
Molecular Weight 155.58
Molecular Formula C7H6ClNO
6-Chloro-3-methylpicolinaldehyde

(9H-fluoren-9-yl)methyl 2-oxoethylcarbamate

CAS 156939-62-7
Catalog BAT-009038
Molecular Weight 281.3
Molecular Formula C17H15NO3
(9H-fluoren-9-yl)methyl 2-oxoethylcarbamate

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.

Online Inquiry

Verification code
Inquiry Basket