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Name	6-Diazo-5-oxonorleucine	EINECS	N/A
CAS No.	157-03-9	Density	g/cm³
PSA	117.78000	LogP	-0.17044
Solubility	N/A	Melting Point	-145oC (dec.)
Formula	C6H9 N3 O3	Boiling Point	°Cat760mmHg
Molecular Weight	171.156	Flash Point	°C
Transport Information	N/A	Appearance	N/A
Safety	Poison by ingestion, intraperitoneal, and intravenous routes. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.	Risk Codes	23/24/25
Molecular Structure		Hazard Symbols	T
Synonyms	Norleucine,6-diazo-5-oxo-, L- (8CI);6-Diazo-5-oxo-L-norleucine;DON;DON(pharmaceutical);L-6-Diazo-5-oxonorleucine;L-DON;NSC 7365;	Article Data	6

6-Diazo-5-oxonorleucine Synthetic route

: 7589-24-4
6-Diazo-5-oxo-N-Tfa-L-norleucine-OMe

: 157-03-9
6-diazo-5-oxo-L-norleucine

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 0.5h; Ambient temperature;	88%

: 208520-02-9
ethyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-diazo-5-oxohexanoate

: 157-03-9
6-diazo-5-oxo-L-norleucine

Conditions

Conditions	Yield
With piperidine for 0.0333333h;	81%

: (S)-N-Fmoc-6-diazo-5-oxo-norleucine

: 157-03-9
6-diazo-5-oxo-L-norleucine

Conditions

Conditions	Yield
With piperidine for 0.0333333h; Inert atmosphere;	52%

: 884594-54-1
(S)-6-diazo-5-oxo-2-(2,2,2-trifluoro-acetylamino)-hexanoic acid ethyl ester

: 157-03-9
6-diazo-5-oxo-L-norleucine

Conditions

Conditions	Yield
With sodium hydroxide

: 42294-25-7
(2S)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanedioic acid α-methyl ester

: 157-03-9
6-diazo-5-oxo-L-norleucine

Conditions

Conditions	Yield
ueber mehrere Stufen;

: (S)-6-Diazo-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-hexanoic acid benzyl ester

: 157-03-9
6-diazo-5-oxo-L-norleucine

Conditions

Conditions	Yield
With piperidine

: 6-diazo-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-hexanoic acid methyl ester

: 157-03-9
6-diazo-5-oxo-L-norleucine

Conditions

Conditions	Yield
With sodium hydroxide

: 71989-18-9
Fmoc-Glu(OtBu)-OH

Fmoc-Leu-OH: Fmoc-Leu-OH

: 157-03-9
6-diazo-5-oxo-L-norleucine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: diethyl ether 2: TFA / CH2Cl2 3: N-methylmorpholine / 0 °C 4: diethyl ether 5: 4M NaOH View Scheme

: 160002-61-9
N-(9-fluorenylmethoxycarbonyl)glutamic acid (O-tert-butyl) methyl ester

: 157-03-9
6-diazo-5-oxo-L-norleucine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: TFA / CH2Cl2 2: N-methylmorpholine / 0 °C 3: diethyl ether 4: 4M NaOH View Scheme

: 145038-49-9
4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid

: 157-03-9
6-diazo-5-oxo-L-norleucine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-methylmorpholine / 0 °C 2: diethyl ether 3: 4M NaOH View Scheme

6-Diazo-5-oxonorleucine Chemical Properties

Molecule structure of 6-Diazo-5-oxonorleucine (CAS NO.157-03-9) :

IUPAC Name: 5-amino-1-diazonio-6-hydroxy-6-oxohex-1-en-2-olate
Molecular Weight: 171.15396 g/mol
Molecular Formula: C₆H₉N₃O₃
Melting Point: ~145 °C (dec.)
Appreance: light yellow crystalline
Merck: 13.3026
XLogP3-AA: -1.5
H-Bond Donor: 2
H-Bond Acceptor: 5
Rotatable Bond Count: 4
Exact Mass: 171.064391
MonoIsotopic Mass: 171.064391
Topological Polar Surface Area: 115
Heavy Atom Count: 12
Complexity: 240
Canonical SMILES: C(CC(=C[N+]#N)[O-])C(C(=O)O)N
InChI: InChI=1S/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H-,10,11,12)
InChIKey: MKZFABOMIIHLIT-UHFFFAOYSA-N
Storage temp.: −20 °C

6-Diazo-5-oxonorleucine Uses

6-Diazo-5-oxonorleucine (CAS NO.157-03-9) exerts a growth inhibitory effect selectively on the neuroendocrine tumour cell line BON and is proposed as an antitumour drug.

6-Diazo-5-oxonorleucine Toxicity Data With Reference

1.	pic-esc 5 µg/plate	CNREA8 Cancer Research. 43 (1983),2819.
2.	ipr-rat LD50:80 mg/kg	CPCHAO Clinical Proceedings of the Childrens Hospital of the District of Columbia. 18 (1962),307.
3.	orl-mus LD50:197 mg/kg	NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program, Bethesda, MD 20205 JAN86 .
4.	ipr-mus LDLo:300 mg/kg	JOENAK Journal of Endocrinology. 18 (1959),204.
5.	ivn-mus LD50:74 mg/kg	85ERAY Antibiotics: Origin, Nature, and Properties. 2 (1978),1253.

6-Diazo-5-oxonorleucine Consensus Reports

EPA Genetic Toxicology Program.

6-Diazo-5-oxonorleucine Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes: Toxic T
Risk Statements: 23/24/25
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed
Safety Statements: 36/37/39-45
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: RC6340000
F: 8

6-Diazo-5-oxonorleucine Specification

6-Diazo-5-oxonorleucine (CAS NO.157-03-9) is also called 6-Diazo-5-oxo,l-norleucin ; 6-Diazo-5-oxo-l-norleucin ; Diazo-oxo-norleucine ; Don(pharmaceutical) ; 6-Diazo-5-oxo-l-2-aminohexanoic acid ; 6-Diazo-5-oxo-l-norleucine ; 6-diazo-5-oxo-norleucine ; L-don .

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