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1-Aminocyclopentanecarboxylic acid

1-Aminocyclopentanecarboxylic acid structure

CAS No:
52-52-8
Formula:
C6H11NO2
Chemical Name:
1-Aminocyclopentanecarboxylic acid
Synonyms:
Cyclopentanecarboxylic acid,1-amino-;1-Aminocyclopentanecarboxylic acid;NSC 1026;1-Aminocyclopentane-1-carboxylic acid;Cycloleucine;ACPC;WR 14997;Cycloleucin;1-Amino-1-carboxycyclopentane;NSC 112194;NSC 112195;NSC 112197;1-Azaniumylcyclopentane-1-carboxylate;15313-85-6
Categories:
Pharmaceutical Intermediates > Gastrointestinal Agents

Description

WHITE TO BEIGE CRYSTALLINE FLAKES OR POWDER

1-aminocyclopentanecarboxylic acid is a non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups. It has a role as an EC 2.5.1.6 (methionine adenosyltransferase) inhibitor.|Cycloleucine is non-metabolisable amino acid formed by cyclization of leucine. It is also a specific and reversible inhibitor of nucleic acid methylation and widely used in biochemical experiments.|Cycloleucine is a non-metabolizable synthetic amino acid, formed through the cyclization of the amino acid leucine, with immunosuppressive, antineoplastic, and cytostatic activities. Cycloleucine competitively inhibits the enzyme methionine adenosyltransferase, resulting in the inhibition of S-adenosylmethionine (SAM) synthesis from methionine and ATP, and subsequent nucleic acid methylation and polyamine production; RNA, and perhaps to a lesser extent, DNA biosyntheses and cell cycle progression are finally disrupted. This agent is also a competitive inhibitor at the glycine modulatory site of the N-methyl-D-aspartate (NMDA) receptor.|An amino acid formed by cyclization of leucine. It has cytostatic, immunosuppressive and antineoplastic activities.

1-Aminocyclopentanecarboxylic acid Basic Attributes

Molecular Weight：

129.16

Exact Mass：

129.16

BRN：

636626

EC Number：

200-144-6

UNII：

0TQU7668EI

NSC Number：

1026

DSSTox ID：

DTXSID5024475

NCI Thesaurus Code：

C404

Color/Form：

CRYSTALS FROM ETHANOL & WATER

HScode：

2922499990

Characteristics

PSA：

63.3

XLogP3：

-2.6

Appearance：

White to beige Crystalline Flakes or Powder

Density：

1.2±0.1 g/cm3

Melting Point：

330 °C (decomp)

Boiling Point：

256.1ºC at 760 mmHg

Flash Point：

108.7±22.6 °C

Refractive Index：

1.522

Water Solubility：

H2O: 5 g/100 mL

Storage Conditions：

Store at RT.

Toxicity：

Oral-rat LD50: 290 mg/kg; Oral-Mouse LD50: 119 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxide fumes

PKA：

2.62None

Dissociation Constants：

2.62

Experimental Properties：

MP 274 °C, DECOMP; PRISMIC CRYSTALS FROM WATER /HYDROCHLORIDE/

Safety Information

Packing level：

III

Hazard category：

6.1

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

safety instructions：

22-24/25

RTECS Number：

GY2625000

Marks：

Xn,Xi

Storage features：

Warehouse ventilated, low temperature and dry

Stability/Shelf Life：

FORMS STABLE METAL SALTS

Precautionary statement(s)：

P301 + P310

Hazard Statements：

H301

GHS Classification：

|Danger|H301 (94.12%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 51 companies from 5 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity class：

highly toxic

Toxicity Summary：

Oral, mouse: LD50 = 309 mg/kg; oral, rat: LD50 = 290 mg/kg

Drug Information

Therapeutic Uses：

EXPTL USE (VET): SINGLE DOSES OF ANTILYMPHOCYTE SERUM, CYCLOPHOSPHAMIDE, CYCLOLEUCINE DELAYED ONSET OF HYPERACUTE FORM OF EXPTL ALLERGIC ENCEPHALOMYELITIS IN RATS. CYCLOLEUCINE & TILORONE-HCL WERE PROVEN TO HAVE SYNERGISTIC RELATIONSHIP.|EXPTL USE: (11)C-CYCLOLEUCINE WAS EVALUATED AS TUMOR SCANNING AGENT IN 38 PT. EXTRAPOLATION FROM ANIMAL DATA GIVES 0.01 RAD/UCI FOR WHOLE BODY & LESS THAN 0.06 RAD/UCI FOR PANCREAS. 33/38 HAS GALLIUM CITRATE (67)GA SCANS ALSO; RESULTS 19 POS FORMER & 24 POS (67)GA SCANS.|MEDICATION (VET): CARBOXYL-LABELED (11)C-CYCLOLEUCINE WAS PREPD IN MULTIMILLICURIE AMT. TISSUE DISTRIBUTION (750 MICROCURIE, IV) IN MORRIS 5123 C HEPATOMA BEARING RATS INDICATED THE COMPD HAS POTENTIAL AS TUMOR-LOCALIZING AGENT FOR DETECTING CANCER IN HUMANS.|MEDICATION (VET): CYCLOLEUCINE PROTECTED RATS AGAINST SEIZURES IN MAXIMAL ELECTROSHOCK TEST BUT OFFERED NO PROTECTION AGAINST METRAZOL-(PENTYLENETETRAZOL) INDUCED SEIZURES IN MICE.

Pharmacology：

Cycloleucine has cytostatic, immunosuppressive and antineoplastic activities.

Absorption：

LEVELS OF (14)C IN LIVER & PANCREAS WERE RESPECTIVELY EIGHTFOLD & TWOFOLD THOSE IN BLOOD, 15 MIN AFTER IV DOSE OF [(14)C]-1-AMINOCYCLOPENTANECARBOXYLIC ACID TO RHESUS MONKEYS. (14)C LEVELS IN THESE TISSUES WERE SIMILAR TO THOSE IN BLOOD AFTER 24 HR.|WHEN ADMIN TO MICE CYCLOLEUCINE ACCUM IN TISSUES AT LEVELS BETWEEN 0.02 & 1.29 MG/ML. MOST OF REMAINING 2% WAS ASSOC WITH PROTEIN. ACCUM AGAINST CONCN GRADIENT OCCURRED IN KIDNEY, IN SPLEEN TO GREATER EXTENT & TO MUCH GREATER DEGREE IN PANCREAS. THE DISTRIBUTION RATIOS FOR CNS TISSUE, KIDNEY & SPLEEN DID NOT CHANGE AS FUNCTION OF PLASMA CYCLOLEUCINE CONCN OR OF TIME BETWEEN 4 & 40 DAYS AFTER ADMIN TO MICE. 5 DAYS AFTER ADMIN OF CYCLOLEUCINE TO MICE, HEPATIC CYCLOLEUCINE DISTRIBUTION RATIO WAS CONSIDERABLY GREATER THAN UNITY AT THE LOWEST DOSES & INCR VARIABLY WITH INCR CYCLOLEUCINE PLASMA LEVELS.

Biological Half-Life：

AT 0.4-0.5 MG/G PLASMA LEVEL AT 24 DAYS WAS NOT SIGNIFICANTLY DIFFERENT FROM THAT AT 1 DAY. HIGHEST DOSES (1-3 MG/G) RESULTED IN NEARLY SIMILAR PLASMA LEVELS BY 4TH DAY. T/2 IN PLASMA WAS EXTREMELY LONG.

Mechanism of Action：

SYNTHETIC AMINO ACID THOUGHT TO ACT AS VALINE ANTAGONIST.

MeSH Entry Terms：

1 Aminocyclopentanecarboxylic Acid

1-Aminocyclopentanecarboxylic acid Use and Manufacturing

Methods of Manufacturing

1- (((9H-Fluoren-9-yl)methoxy)carbonylamino)cyclopentanecarboxylic acid(compound 4 of example A): Fmoc-OSu (3.13 g, 9.3 mmol) was added to a solution of 1- aminocyclo- pentanecarboxylic acid (1.0 g, 7.8 mmol) and NaHC03 (1.63 g, 19.4 mmol) in acetonitrile/water (100 mL, 1 : 1). The reaction mixture was stirred at room temperature overnight. Most of the solvent was removed under reduced pressure and the resulting mixture was adjusted to pH = 2 with 2 N HCI and extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (PE/EA = 20: 1) to afford compound 4 of example A (0.75 g, 28% yield) as a white solid.General procedure: To 250 mL round-bottomed flask add 1a or 1c or 1g or 1h, 2.5 equiv Fmoc-OSu, 50 mL THF/H2O (1:1, v/v), pH of the solution was adjusted with saturated sodium carbonate to 8-9, and the reaction continued at room temperature for about 18h. After that, the solution was extracted twice with ether, and pH of aqueous layer was adjusted with concentrated HCl to 5, white precipitation was obtain and dried in vacuum to gave corresponding product (2a or 2c or 2g or 2h).

Uses

A synthetic amino acid used in numerous biochemical transport studies

Manufacturing Info：

Cyclopentanecarboxylic acid, 1-amino-: ACTIVE

Computed Properties

Molecular Weight:129.16
XLogP3:-2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:129.078978594
Monoisotopic Mass:129.078978594
Topological Polar Surface Area:63.3
Heavy Atom Count:9
Complexity:127
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of 1-Aminocyclopentanecarboxylic acid

Description
Basic Attributes
Characteristics
Safety Information
Toxicity
Drug Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
Latest News
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1-Aminocyclopentanecarboxylic acid

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