(-)-Azetidinecarboxylic acid

101.1

101.10

218-362-5

5GZ3E0L9ZU

DTXSID0044020

CRYSTALS FROM 95% HOT METHANOL

2933990090

49.3

-2.9

Beige crystals.

1.3±0.1 g/cm3

212 °C (decomp)

224ºC

100.1±25.4 °C

1.499

5 g/100 mL

2-8ºC

0.0116mmHg at 25°C

LD50 scu-mus: 1000 mg/kg 85GDA2 8(1),101,82

SPECIFIC OPTICAL ROTATION (WATER C= 3.6): -108 DEG @ 20 °C/D ACIDS

DISCOLORS AT 200 °C & DARKENS UNTIL 310 °C WHEN HEATING STOPPED; UNSTABLE TO MINERAL ACIDS

NONH for all modes of transport

3

R36/37/38

S24/25

CM4310500

Xi

Stable under normal temperatures and pressures.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

THE CHRONIC ADMINISTRATION OF CARBON TETRACHLORIDE TO RATS INDUCED CIRRHOSIS AND INCREASED ALBUMIN SYNTHESIS, BUT SIMULTANEOUS ADMIN OF CARBON TETRACHLORIDE WITH L-AZETIDINE-2-CARBOXYLIC ACID DECR ALBUMIN SYNTHESIS AND ELICITED A RETURN OF SERUM ALBUMIN LEVELS TO NORMAL VALUES.|L-AZETIDINE-2-CARBOXYLIC ACID SEVERELY INHIBITED THE INDUCTION OF NITRATE REDUCTASE BY NITRATE IN RADISH AND CAULIFLOWER LEAF TISSUES WITH A LOW L-PROLINE CONTENT. INHIBITION WAS REVERSED BY SIMULTANEOUS INFILTRATION OF L-PROLINE.

FROM CONVALLARIA MAJALIS L (LILY-OF-THE-VALLEY) & POLYGONATUM OFFICINALE MOENSH, LILIACEAE: FOWDEN, BIOCHEM J 64, 323 (1956); FOWDEN, BRYANT, BIOCHEM J 70, 626 (1958).

ALLYLGLYCINE (0.1 MMOL) INHIBITED THE UPTAKE OF 0.1 UMOL 4,5-(3)H-LABELED L-LEUCINE (1 CURIE/MMOLE) AND U-(3)H-LABELED L-PROLINE (266 MCI/MMOLE) BY RAT BRAIN SLICES. LEUCINE UPTAKE WAS NOT LINEAR WITH TIME; PROLINE UPTAKE WAS ALSO INHIBITED BY L-AZETIDINE-2-CARBOXYLIC ACID.|L-AZETIDINE-2-CARBOXYLIC ACID WAS POTENT IN CAUSING AMNESIA OF 1-TRIAL AVOIDANCE CONDITIONING OF THE 2-DAY-OLD CHICK AND IN PREVENTING MECHANICALLY INDUCED SPREADING DEPRESSION IN THE RETINA ISOLATED FROM 2-3 WK-OLD CHICKS. L-AZETIDINE-2-CARBOXYLIC ACID IS INCORPORATED INTO PROTEIN IN PLACE OF L-PROLINE IN SEVERAL PROTEIN-SYNTHESIZING SYSTEMS.|THE ADDITION OF L-AZETIDINE-2-CARBOXYLIC ACID TO THE INCUBATION MEDIUM OF FETAL RAT CALVARIA DECREASED THE INTRACELLULAR FREE PROLINE AND THE RATES OF PROLINE INCORPORATION INTO PROTEIN AND COLLAGEN BY 40-70%. THE ALTERATIONS IN INTRACELLULAR PROLINE CONCN PRODUCED EITHER BY VARYING EXTRACELLULAR PROLINE CONCN OR BY INHIBITING THE UPTAKE OF PROLINE INTO THE INTRACELLULAR POOL MAY CONTRIBUTE TO THE REGULATION OF COLLAGEN SYNTHESIS.|PROLINE PERMEASE FROM PSEUDOMONAS AERUGINOSA OBEYED SATURATION KINETICS & WAS SPECIFIC FOR L-PROLINE. L-AZETIDINE-2-CARBOXYLIC ACID COMPETITIVELY INHIBITED PROLINE UPTAKE. IT WAS ALSO ABLE TO EXCHANGE WITH A PRE-ESTABLISHED LABELED PROLINE INTRACELLULAR POOL.|SIXTEEN-DAY-OLD MOUSE EMBRYONIC ODONTOBLASTS, TREATED FOR 4 DAYS WITH L-2-AZETIDINECARBOXYLIC ACID (50, 100, & 200 GAMMA) WERE POST-MITOTIC, BUT NONPOLARIZED AND DID NOT SECRETE PICROFUCHSIN-POSITIVE SUBSTANCES (COLLAGEN). 18-DAY-OLD EMBRYONIC ODONTOBLASTS TREATED WITH L-2-AZETIDINECARBOXYLIC CONTAINED NO PICROFUCHSIN-POSITIVE SUBSTANCES AND NO COLLAGEN FIBERS OF STRIATION; PREADAMANTOBLASTS WERE POST-MITOTIC BUT NONPOLARIZED.

INCUBATION OF HUMAN SKIN FIBROBLASTS IN CULTURE WITH L-AZETIDINE-2-CARBOXYLIC ACID (LACA) REDUCED THE RATE OF FIBROBLAST PROLIFERATION AND LOWERED THE PLATING EFFICIENCY. FIBROBLASTS SYNTHESIZED PROCOLLAGEN POLYPEPTIDES WHICH WERE NOT IN A TRIPLE-HELICAL CONFORMATION. THE PROLINE ANALOGS THUS APPEAR TO INHIBIT THE PRODUCTION OF PROCOLLAGEN ON THE POST-TRANSLATIONAL LEVEL BY PREVENTING THE POLYPEPTIDES FROM FOLDING INTO A STABLE TRIPLE-HELICAL CONFORMATION. INHIBITION OF PROCOLLAGEN WAS NOTED IN SCLERODERMA CELLS AS WITH CONTROL FIBROBLAST CULTURES. PROLINE ANALOGS MAY BE USEFUL IN LIMITING EXCESSIVE COLLAGEN DEPOSITION IN SCLERODERMA AND OTHER FORMS OF DERMAL FIBROSIS.

azetidyl-2-carboxylic acid

ACTS AS A PROLINE ANALOG WHERE A STOICHIOMETRIC REPLACEMENT OF PROLINE OCCURRED WITH PRODN OF ABNORMAL PROTEINS HAVING IMPAIRED BIOLOGICAL ACTIVITY...