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Cyclic Amino Acids

3-Amino-adamantane-1-carboxylic acid

CAS 6240-10-4
Catalog BAT-014222
Molecular Weight 195.26
Molecular Formula C11H17NO2
3-Amino-adamantane-1-carboxylic acid

Boc-4-amino-3-methoxybenzoic acid

CAS 180976-98-1
Catalog BAT-014226
Molecular Weight 267.28
Molecular Formula C13H17NO5
Boc-4-amino-3-methoxybenzoic acid

3-Aminobenzoic Acid

CAS 99-05-8
Catalog BAT-014273
Molecular Weight 137.14
Molecular Formula C7H7NO2
3-Aminobenzoic Acid

Boc-O-benzyl-L-trans-4-hydroxyproline dicyclohexylammonium salt

Catalog BAT-014275
Molecular Weight 502.7
Molecular Formula C17H23NO5.C12H23N
Boc-O-benzyl-L-trans-4-hydroxyproline dicyclohexylammonium salt

Pyrrole-2-carboxylic acid

CAS 634-97-9
Catalog BAT-014290
Molecular Weight 111.10
Molecular Formula C5H5NO2
Pyrrole-2-carboxylic acid

Methyl L-pyroglutamate

CAS 4931-66-2
Catalog BAT-014304
Molecular Weight 143.14
Molecular Formula C6H9NO3
Methyl L-pyroglutamate

L-Hydroxyproline

CAS 51-35-4
Catalog BAT-014305
Molecular Weight 131.13
Molecular Formula C5H9NO3
L-Hydroxyproline

L-Proline

CAS 147-85-3
Catalog BAT-014310
Molecular Weight 115.13
Molecular Formula C5H9NO2
L-Proline

Bz-Arg-4-Abz-OH·HCl

CAS 60833-82-1
Catalog BAT-014335
Molecular Weight 397.43
Molecular Formula C20H23N5O4
Bz-Arg-4-Abz-OH·HCl

1-Methyl-1H-imidazole-2-carboxylic acid

CAS 20485-43-2
Catalog BAT-014391
Molecular Weight 126.11
Molecular Formula C5H6N2O2
1-Methyl-1H-imidazole-2-carboxylic acid

(3S,4R)-4-(4-Chlorophenyl)-3-pyrrolidinecarboxylic acid

CAS 1047651-82-0
Catalog BAT-015012
Molecular Weight 225.67
Molecular Formula C11H12ClNO2
(3S,4R)-4-(4-Chlorophenyl)-3-pyrrolidinecarboxylic acid

(3S,4R)-4-(4-Methoxyphenyl)-3-pyrrolidinecarboxylic acid

CAS 1049978-93-9
Catalog BAT-015013
Molecular Weight 221.25
Molecular Formula C12H15NO3
(3S,4R)-4-(4-Methoxyphenyl)-3-pyrrolidinecarboxylic acid

Fmoc-D-Pro-OH

CAS 101555-62-8
Catalog BAT-015020
Molecular Weight 337.37
Molecular Formula C20H19NO4
Fmoc-D-Pro-OH

L-Homoserine lactone hydrochloride

CAS 2185-03-7
Catalog BAT-015024
Molecular Weight 137.56
Molecular Formula C4H7NO2.HCl
L-Homoserine lactone hydrochloride

D-Homocysteine Lactone HCl

CAS 104347-13-9
Catalog BAT-015038
Molecular Weight 137.56
Molecular Formula C4H7NO2.HCl
D-Homocysteine Lactone HCl

DL-Pipecolinic acid

CAS 4043-87-2
Catalog BAT-015039
Molecular Weight 129.16
Molecular Formula C6H11NO2
DL-Pipecolinic acid

Methyl aziridine-2-carboxylate

CAS 5950-34-5
Catalog BAT-015044
Molecular Weight 101.10
Molecular Formula C4H7NO2
Methyl aziridine-2-carboxylate

Isonipecotic acid

CAS 498-94-2
Catalog BAT-015048
Molecular Weight 129.16
Molecular Formula C6H11NO2
Isonipecotic acid

1H-Pyrazole-1-carboxamidine hydrochloride

CAS 4023-02-3
Catalog BAT-015051
Molecular Weight 146.58
Molecular Formula C4H6N4.HCl
1H-Pyrazole-1-carboxamidine hydrochloride

N-Methyl-L-proline monohydrate

CAS 199917-42-5
Catalog BAT-015054
Molecular Weight 147.17
Molecular Formula C6H13NO3
N-Methyl-L-proline monohydrate

Cyclic amino acids (Accn), where n represents the number of carbon atoms in the ring (Figure 1).

Cyclic Amino Acids

Cyclic amino acids are configuration-limited amino acids; Cyclic amino acids play an important role in the design and synthesis of bioactive peptides because of their structural rigidity, which can cause important conformational effects. Cyclic amino acids are often used in the sequence of polypeptides to find economic, efficient and bioactive peptides resistant to enzymatic degradation. They are also used in DNA or peptide nucleic acid (PNA) to stabilize their helix structure, which has a good application prospect in botany, biology, anti-inflammatory drugs, anti-tumor drugs, cancer cell detection and other aspects.

Application of Cyclic Amino Acids

1. Plant growth hormone regulator

Acc3 widely exists in the fruits of plants, is a new plant growth regulator, can be converted into ethylene under the action of enzymes, fruits, vegetables, tomatoes and other obvious ripening effect, has great economic significance in agriculture.

2. Anti-inflammatory activity

Acc6 can be used for the design and synthesis of anti-inflammatory drugs. For example: The tripeptide Formyl-Met-Acc6-Phe-OH can induce the release of pharmacotaxis and dissolution of neutrophils, so that the peptide chain can bind to the receptor on the surface of neutrophils and have anti-inflammatory activity. Formyl-Met-Acc6-Phe-OH replaced by Acc6 has stronger biological activity. Polypeptide analogues synthesized from cyclic amino acids are many times more active than the parent peptide. In addition, NMR and modeling studies showed that polypeptide analogues synthesized using cyclic amino acids were more likely to form β -rotation in solution, and were more easily recognized by neutrophil receptors and had better drug activity.

3. Antidiuretic activity

At the same time, Acc6 can also be used in the study of antidiuretic active drugs. For example: the use of Acc6 to replace the 2 or 3 amino acids of agonists of Arginine vasopressin (AVP) can play a role in narrowing blood vessels, promoting the rise of blood pressure and producing good antidiuretic activity. In addition, the introduction of configuration-limited nitrogenous acid Acc can reduce the flexibility of peptide chain and limit the degree of freedom of the conformation of peptide chain. Forcing peptide chains and residues into specific positions can prevent protein hydrolysis and increase protein stability.

4. Antitumor activity

Acc5 has the activity of inhibiting tumor growth. The tumor suppressor gene p53 is a multifunctional protein, which can regulate cell proliferation and inhibit the growth of cancer cells by inhibiting cell growth or causing cell apoptosis, DNA damage or stress stress.

When the glycine at the 7th position in the p53 protein polypeptide chain is replaced by Acc5, the p53 protein can more easily bind to the hydrophobic pocket of hdm2 receptor, thus strengthening the binding force with hdm2 receptor, better regulating the protein expression of p53 and inhibiting the growth of cancer cells.

5. Treatment of cardiovascular diseases

The introduction of cyclic amino acids into peptide sequences can make peptide sequences act as angiotensin converting enzyme (ACE) inhibitors and neutral endopeptidase (NEP) inhibitors. Cyclic amino acid modification of synthetic peptide sequences is useful for the treatment of diseases associated with ACE or NEP inhibitors, especially cardiovascular disorders such as hypertension, renal failure (including floating fibular and salt depletion), pulmonary edema, and congestive heart failure.

6. Cancer detection

Acc5 can be used in the diagnosis of cancer. For example, after injection of 11C-labeled radioactive Acc5 for 1h, the accumulation of radioactive Acc5 in cancer cells was significantly higher than that in liver, and the distribution ratio between cancer cells and liver could reach 3:1.Using radioactive Acc5 for cancer cell detection found that Acc5 and cancer cells have a strong binding force, under X-ray diffraction, can be very good imaging, in the early diagnosis of brain tumor has a good prospect.

7. Others

Using Acc6 to replace Ala in tetradeceptide chain, tetradeceptide can be reduced to decapeptide, and the antibacterial activity of decapeptide can reach 8 ~ 10 times that of parent peptide. At the same time, cyclic amino acids can also be used as fungicides and sweeteners.

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