Amino Acids for Stapled Peptide

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Amino Acids for Stapled Peptide

(S)-N-BOC-allylglycine

CAS 90600-20-7
Catalog BAT-006509
Molecular Weight 215.24
Molecular Formula C10H17NO4
(S)-N-BOC-allylglycine

(2S)-2-Amino-6-heptenoic acid

CAS 166734-64-1
Catalog BAT-006512
Molecular Weight 143.18
Molecular Formula C7H13NO2
(2S)-2-Amino-6-heptenoic acid

(S)-2-Aminooct-7-enoic acid

CAS 1140737-02-5
Catalog BAT-006513
Molecular Weight 157.21
Molecular Formula C8H15NO2
(S)-2-Aminooct-7-enoic acid

(2S)-2-Amino-8-nonenoic acid

CAS 924307-76-6
Catalog BAT-006514
Molecular Weight 171.24
Molecular Formula C9H17NO2
(2S)-2-Amino-8-nonenoic acid

2-Allyl-D-proline hydrochloride

CAS 129704-91-2
Catalog BAT-006724
Molecular Weight 191.65
Molecular Formula C8H14ClNO2
2-Allyl-D-proline hydrochloride

2-Allyl-L-proline hydrochloride

CAS 177206-69-8
Catalog BAT-006725
Molecular Weight 191.65
Molecular Formula C8H14ClNO2
2-Allyl-L-proline hydrochloride

2-Propynyl-D-proline hydrochloride

CAS 1217828-88-0
Catalog BAT-006763
Molecular Weight 189.64
Molecular Formula C8H12ClNO2
2-Propynyl-D-proline hydrochloride

2-Propynyl-L-proline hydrochloride

CAS 1049733-10-9
Catalog BAT-006764
Molecular Weight 189.64
Molecular Formula C8H12ClNO2
2-Propynyl-L-proline hydrochloride

D-α-Allylglycine hydrochloride

CAS 108412-04-0
Catalog BAT-006863
Molecular Weight 151.59
Molecular Formula C5H10ClNO2
D-α-Allylglycine hydrochloride

N-α-Carbobenzoxy-L-α-allylglycine

CAS 78553-51-2
Catalog BAT-006923
Molecular Weight 249.27
Molecular Formula C13H15NO4
N-α-Carbobenzoxy-L-α-allylglycine

N-γ-Allyloxycarbonyl-γ-aminobutyric acid

CAS 80127-29-3
Catalog BAT-006950
Molecular Weight 187.20
Molecular Formula C8H13NO4
N-γ-Allyloxycarbonyl-γ-aminobutyric acid

trans-4-Allyl-L-proline hydrochloride

CAS 1049755-14-7
Catalog BAT-007005
Molecular Weight 191.65
Molecular Formula C8H14ClNO2
trans-4-Allyl-L-proline hydrochloride

trans-4-Propynyl-L-proline hydrochloride

CAS 1049755-32-9
Catalog BAT-007008
Molecular Weight 189.64
Molecular Formula C8H11NO2HCl
trans-4-Propynyl-L-proline hydrochloride

β-Allyl-D-β-homoglycine hydrochloride

CAS 332064-79-6
Catalog BAT-007531
Molecular Weight 165.62
Molecular Formula C6H12ClNO2
β-Allyl-D-β-homoglycine hydrochloride

L-Glutamic acid diallyl ester tosylate

CAS 20845-16-3
Catalog BAT-007700
Molecular Weight 399.46
Molecular Formula C11H17NO4·C7H8O3S
L-Glutamic acid diallyl ester tosylate

Nα-Allyloxycarbonyl-L-phenylalanine dicyclohexylammonium salt

CAS 110637-43-9
Catalog BAT-007724
Molecular Weight 430.60
Molecular Formula C13H15NO4·C12H23N
Nα-Allyloxycarbonyl-L-phenylalanine dicyclohexylammonium salt

Nα-Fmoc-L-histidine allyl ester

CAS 220932-33-2
Catalog BAT-007729
Molecular Weight 417.46
Molecular Formula C24H23N3O4
Nα-Fmoc-L-histidine allyl ester

Nα-Fmoc-L-lysine allyl ester hydrochloride

CAS 815619-80-8
Catalog BAT-007730
Molecular Weight 444.96
Molecular Formula C24H28N2O4·HCl
Nα-Fmoc-L-lysine allyl ester hydrochloride

Z-L-aspartic acid β-allyl ester

CAS 99793-10-9
Catalog BAT-007758
Molecular Weight 307.30
Molecular Formula C15H17NO6
Z-L-aspartic acid β-allyl ester

L-Allylglycine

CAS 16338-48-0
Catalog BAT-008135
Molecular Weight 115.1
Molecular Formula C5H9NO2
L-Allylglycine

Amino acids for stapled peptide are a special class of non-natural amino acids, usually containing α -methyl and α -alkene groups. The olefin redecomposition reaction occurs between these two kinds of non-natural amino acids, cyclizing to form stable α -helix conformation of all carbon scaffold, and then synthesizing stapled peptide.

General structure of two  types of amino acids for stapled peptide Fig.1 General structure of two types of amino acids for stapled peptide

Amino acids for stapled peptide have the characteristics of strong site specificity, wide range of substrates, small disturbance to protein structure and flexible use. Amino acids for stapled peptide are widely used in genetic engineering, biology, medicine, pharmacy, chemistry and other research.

Application of amino acids for stapled peptide

1. Application in genetic engineering

Amino acids for stapled peptide have many applications in genetic engineering drugs based on recombinant proteins, including recombinant cytokines, protein hormones, recombinant plasma proteins, recombinant thrombotic drugs, soluble receptors, therapeutic antibodies, recombinant medicinal plant and animal proteins, etc. Meanwhile, amino acids for stapled peptide can also be used in biological drugs and vaccines for prevention or therapy, nucleic acid drugs, small molecule polypeptide drugs, etc.

Amino acids for stapled peptide have more flexible and diverse R groups than other amino acids. Amino acids with different side chain pKa and REDOX potentials for stapled peptide can be used in kinetic studies. In addition, many amino acids for stapled peptide are used to detect protein-protein interactions due to their protein crosslinking properties.

2. Applications in biology and medicine

Because amino acids for stapled peptide have the ability to insert proteins precisely, it makes it possible for scientists to manipulate the structure of large molecules of drugs as precisely as they do in small molecules. This shows that amino acids for stapled peptide have great application prospect in bio-medicine.

For example, amino acids for stapled peptide are bioorthogonal, improving the targeting specificity and efficacy of drugs. Proteins containing amino acids for stapled peptide (e.g. cytokines, growth factors, antibodies) are specifically linked to other modules to form pegylated proteins, antibody-drug conjugates, antibody-antisense oligonucleotide conjugates, bi-specific antibodies, etc.

Incorporating amino acids for stapled peptide into protein sequences is a strategy for designing new proteins in synthetic biology. This strategy is important for studying the folding and function of natural proteins. In addition, amino acids for stapled peptide are also widely used as initial modular building units in the total synthesis of natural products.

3. Application in pharmacy

Amino acids for stapled peptide are also important drugs in their own right, and they are important structural units of many commercially available drugs. Amino acids for stapled peptide are widely used in anti-bacterial, anti-inflammatory, anti-convulsant, anti-cell growth and anti-tumor drugs, and most of these drugs have entered clinical studies. For pharmaceutical companies, no one can ignore the role of amino acids for stapled peptide in the development of new drugs. Amino acids for stapled peptide are also widely used in proteins, nucleosides and nucleic acids. They can limit the conformational flexibility of peptides, provide DNA or RNA molecules with stable secondary structures, enhance enzyme stability of peptides, and improve pharmacokinetic and biological activity.

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