2219-31-0

Usage

Uses

Used in Pharmaceutical Industry:
L-CANAVANINE SULFATE is used as a Nitric Oxide Synthase inhibitor for its potential therapeutic effects in various medical conditions.
Used in Molecular Biology Research:
L-CANAVANINE SULFATE is used as a translation inhibitor in yeast translation studies, aiding in the understanding of protein synthesis mechanisms.
Used in Genetic Research:
L-CANAVANINE SULFATE is used as a component of synthetic complete (SC) drop-out medium for screening yeast, which helps in identifying specific genetic mutations and their effects on cellular processes.
Used in Canavanine Mutation Frequency Assay:
L-CANAVANINE SULFATE is used for screening Saccharomyces cerevisiae in canavanine mutation frequency assay, which is crucial for studying the genetic stability and mutation rates in yeast populations.

Biochem/physiol Actions

Canavanine is a naturally occurring?L-amino acid that competes and interferes with?L-arginine-utilizing enzymes due to its structural similarity with this?L-amino acid. It is a selective inhibitor of inducible nitric oxide synthase (iNOS). It acts as a substrate for arginyl tRNA and is incorporated during protein synthesis leading to aberrant canavanyl proteins. Supplementation with canavanine worsens the alfalfa induced Systemic lupus erythematosus (SLE) like syndrome and its incorporation with endosome and proteasome disrupts the antigen processing.

Purification Methods

Recrystallise the sulfate by dissolving (~1g) in H2O (10mL), and adding with stirring 0.5 to 1.0 volumes of 95% EtOH whereby crystals separate. These are collected, washed with Me2CO/EtOH (1:1) and dried over P2O5 in a vacuum. [Hunt & Thompson Biochemical Preparations 13 416 1971, Feacon & Bell Biochem J 59 221 1955, Beilstein 4 III 1636, 4 IV 3188.]

InChI:InChI=1/C5H12N4O3.H2O4S/c6-3(4(10)11)1-2-12-9-5(7)8;1-5(2,3)4/h3H,1-2,6H2,(H,10,11)(H4,7,8,9);(H2,1,2,3,4)/t3-;/m0./s1

Synthetic route

methanol (67-56-1) + (-)-canavaninium sulfate (2219-31-0) → NH2-Cav-OMe dihydrochloride (142154-80-1)

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 18h; Inert atmosphere;	99%

potassium hexafluorophosphate (17084-13-8) + chloro(2,2':6',2''-terpyridine)platinum(II) chloride dihydrate + (-)-canavaninium sulfate (2219-31-0) → {(Pt(2,2':6',2''-terpyridine))2(L-canavanine)}(PF6)3

Conditions	Yield
In water Pt-complex, the guanidine kept at 40°C, 4d, pH adjusted to ca 9.0 with 1M NaOH, chromy. (cation exchanger CM52; elution: potassium phosphate buffer pH7.0), evapn. (vac.) to conc. vol., satd. aq. soln. of KPF6 added, left at 4°C, red pptn.; filtered, washed (cold MeOH, cold OEt2), elem. anal.;	92%

chloro(2,2':6',2''-terpyridine)platinum(II) chloride dihydrate + (-)-canavaninium sulfate (2219-31-0) → {Pt(2,2':6',2''-terpyridine)(L-canavanine)}Cl2 + {(Pt(2,2':6',2''-terpyridine))2(L-canavanine)}Cl3

Conditions	Yield
In water Pt-complex, the guanidine in potassium phosphate buffer of pH 8.5 kept at 40°C, 9h, color change from orange to deep red; filtered, evapn. to minimum of vol., chromy. (CM52 cation exchanger; elution with potassium phosphate buffer pH 8.5 first at 4°C, then at room temp.);

(-)-canavaninium sulfate (2219-31-0) → Cbz-Cav(N,N-Boc)-OMe

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / 18 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / water; tetrahydrofuran / 1 h / 20 °C 3: triethylamine / water; tetrahydrofuran / 18 h / 20 °C View Scheme

(-)-canavaninium sulfate (2219-31-0) → Cbz-Cav(N,N-Boc)-OH (319910-81-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / 18 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / water; tetrahydrofuran / 1 h / 20 °C 3: triethylamine / water; tetrahydrofuran / 18 h / 20 °C 4: lithium hydroxide monohydrate; water / tetrahydrofuran / 4 h / 20 °C View Scheme

(-)-canavaninium sulfate (2219-31-0) → WEHI-842

Conditions

Yield

Multi-step reaction with 6 steps 1.1: thionyl chloride / 18 h / 0 - 20 °C / Inert atmosphere 2.1: triethylamine / water; tetrahydrofuran / 1 h / 20 °C 3.1: triethylamine / water; tetrahydrofuran / 18 h / 20 °C 4.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 4 h / 20 °C 5.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 5.2: 18 h / 20 °C 6.1: dichloromethane / 18 h / 20 °C View Scheme

(-)-canavaninium sulfate (2219-31-0) → Cbz-Cav(N,N-Boc)-Val-Sta-NH(CH2)2Ph

Conditions

Yield

Multi-step reaction with 5 steps 1.1: thionyl chloride / 18 h / 0 - 20 °C / Inert atmosphere 2.1: triethylamine / water; tetrahydrofuran / 1 h / 20 °C 3.1: triethylamine / water; tetrahydrofuran / 18 h / 20 °C 4.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 4 h / 20 °C 5.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 5.2: 18 h / 20 °C View Scheme

(-)-canavaninium sulfate (2219-31-0) → Cbz-Cav-OMe

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 18 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / water; tetrahydrofuran / 1 h / 20 °C View Scheme