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Azido Amino Acids

(2S,4S)-Fmoc-4-azido-pyrrolidine-2-carboxylic acid

CAS 263847-08-1
Catalog BAT-007616
Molecular Weight 378.39
Molecular Formula C20H18N4O4
(2S,4S)-Fmoc-4-azido-pyrrolidine-2-carboxylic acid

2-(R)-Fmoc-amino-3-azidopropionic acid

CAS 1016163-79-3
Catalog BAT-007622
Molecular Weight 352.30
Molecular Formula C18H16N4O4
2-(R)-Fmoc-amino-3-azidopropionic acid

4-(4-Azidophenyl)butyric acid

CAS 103489-33-4
Catalog BAT-007623
Molecular Weight 205.22
Molecular Formula C10H11N3O2
4-(4-Azidophenyl)butyric acid

8-Azido-3,6-dioxaoctanoic acid cyclohexylammonium salt

CAS 2098500-94-6
Catalog BAT-007625
Molecular Weight 288.34
Molecular Formula C12H24N4O4
8-Azido-3,6-dioxaoctanoic acid cyclohexylammonium salt

8-Azido-3,6-dioxaoctanoic acid tert-butyl ester

CAS 251564-45-1
Catalog BAT-007626
Molecular Weight 245.28
Molecular Formula C10H19N3O4
8-Azido-3,6-dioxaoctanoic acid tert-butyl ester

Azido myristic acid

CAS 80667-36-3
Catalog BAT-007628
Molecular Weight 241.33
Molecular Formula C12H23N3O2
Azido myristic acid

L-2-(Fmoc-amino)-4-azidobutanoic acid

CAS 942518-20-9
Catalog BAT-007696
Molecular Weight 366.38
Molecular Formula C19H18N4O4
L-2-(Fmoc-amino)-4-azidobutanoic acid

Nα-Azido-Nε-Boc-L-Lysine

CAS 333366-32-8
Catalog BAT-007725
Molecular Weight 272.30
Molecular Formula C11H20N4O4
Nα-Azido-Nε-Boc-L-Lysine

Nα-Fmoc-Nγ-Azido-D-2,4-diaminobutyric acid

CAS 1263047-53-5
Catalog BAT-007734
Molecular Weight 366.40
Molecular Formula C19H18N4O4
Nα-Fmoc-Nγ-Azido-D-2,4-diaminobutyric acid

Nα-Fmoc-Nδ-Azido-D-Ornithine

CAS 1176270-25-9
Catalog BAT-007736
Molecular Weight 380.40
Molecular Formula C20H20N4O4
Nα-Fmoc-Nδ-Azido-D-Ornithine

Nα-Fmoc-Nε-azide-L-Lysine

CAS 159610-89-6
Catalog BAT-007737
Molecular Weight 394.42
Molecular Formula C21H22N4O4
Nα-Fmoc-Nε-azide-L-Lysine

Nα-Fmoc-Nε-Azido-D-Lysine

CAS 1198791-53-5
Catalog BAT-007738
Molecular Weight 394.42
Molecular Formula C21H22N4O4
Nα-Fmoc-Nε-Azido-D-Lysine

Nα-Z-Nγ-Azido-L-2,4-diaminobutyric acid dicyclohexylamine salt

CAS 1263047-43-3
Catalog BAT-007745
Molecular Weight 459.59
Molecular Formula C12H14N4O4·C12H23N
Nα-Z-Nγ-Azido-L-2,4-diaminobutyric acid dicyclohexylamine salt

Nβ-Azido-D-2,3-diaminopropionic acid hydrochloride

CAS 1379690-01-3
Catalog BAT-007746
Molecular Weight 166.57
Molecular Formula C3H7ClN4O2
Nβ-Azido-D-2,3-diaminopropionic acid hydrochloride

Nγ-Azido-L-2,4-diaminobutyric acid hydrochloride

CAS 942518-29-8
Catalog BAT-007747
Molecular Weight 180.59
Molecular Formula C4H8N4O2·HCl
Nγ-Azido-L-2,4-diaminobutyric acid hydrochloride

Nδ-Azido-D-Ornithine hydrochloride

CAS 156463-09-1
Catalog BAT-007748
Molecular Weight 194.60
Molecular Formula C5H11ClN4O2
Nδ-Azido-D-Ornithine hydrochloride

Nε-Azido-L-Lysine hydrochloride

CAS 1454334-76-9
Catalog BAT-007749
Molecular Weight 208.60
Molecular Formula C6H13ClN4O2
Nε-Azido-L-Lysine hydrochloride

sulfo-Succinimidyl-6-[(4'-azido-nitrophenyl)amino]hexanoate

CAS 102568-43-4
Catalog BAT-007754
Molecular Weight 470.41
Molecular Formula C16H18N6O9S
sulfo-Succinimidyl-6-[(4'-azido-nitrophenyl)amino]hexanoate

Boc-ε-azido-Nle-OH

CAS 846549-33-5
Catalog BAT-015383
Molecular Weight 272.31
Molecular Formula C11H20N4O4
Boc-ε-azido-Nle-OH

H-γ-azido-Abu-OH

CAS 120042-14-0
Catalog BAT-015384
Molecular Weight 144.13
Molecular Formula C4H8N4O2
H-γ-azido-Abu-OH

Azides act as powerful synthetic tools capable of binding to biological macromolecules and selectively modifying enzymes, cells, viral particles, proteins and tissue lysates. Azido amino acids are valuable synthetic building blocks for peptide chemistry, biomacromolecules incorporation, etc.

Application of Azide Amino Acids

1. Application of Antibody-Drug Site-Specific Conjugation

Antibody-drug site-specific coupling can be achieved by introducing azido amino acids. Commonly used azido amino acids include azide-methyl-L-phenylalanine and azide-lysine. Antibodies introduced with azido amino acids can be fixed and quantitatively coupled to drug linkers to obtain antibody-drug couples with uniform drug-antibody ratios, high potency, stability and safety. An example is a Her2/neu antibody containing four different azido-lysine sites, each of which is capable of binding to either toxin auristatin For Pyrrolobenzodiazepines (PBD) dimer to produce an antibody-bound drug with a drug to antibody ratio greater than 1.9.

2. Application of Structural Studies of Proteins

The real-time observation of structural changes associated with protein function is of great research importance. The unnatural amino acid azidophenylalanine was introduced into the light-activated protein. As a probe, azidophenylalanine is able to reveal the changing characteristics and and dynamic nature of the light-driven structure of the protein. In addition, the azidophenylalanine conjugate has an azide asymmetric stretching vibrational extinction coefficient and high environmental response sensitivity. It is commonly used in the study of protein conformational properties due to its ability to detect protein hydration with high spatial resolution.

3. Application of Targeted Modification of Biomolecules

The introduction of amino acids with azide groups in proteins can provide specific reaction sites for the targeted modification of protein drugs. This has important implications for the design and development of novel biotechnology products.

Azidohomoalanine is a methionine analog that is well tolerated for protein binding in the body. By introducing azidohomoalanine in vivo, the original methionine in the viral structural protein was replaced. Azidohomoalanine-modified viral proteins are expressed and assembled into viral particles. The assembled virus particles can be detected at the single particle level, while the original normal methionine-containing virus particles cannot be detected. Thus, azide amino acids can modify viral proteins, which is useful for studying virion structure and virus-host interactions.

PEG modifiers mostly target lysine residues within proteins and do not selectively target specific sites for modification, which usually causes a reduction in protein activity and is detrimental to in vivo drug delivery. Targeted PEG modification of proteins can be achieved by the specific introduction of azido amino acids and their specific reaction with alkyne groups.

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