Available from stock

N-Z-L-Homoserine lactone

SKU: H0379

Category: Building Blocks, Intermediates, Reagents

Synonyms: N-Benzyloxycarbonyl-L-homoserine Lactone, N-Cbz-L-Homoserine lactone, N-Carbobenzoxy-L-homoserine Lactone, (S)-&alpha,-(Cbz-amino)-&gamma,-butyrolactone; 35677-89-5
CAS-Number: C₁₂H₁₃NO₄
Molecular Formula: 235.24
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥95% (NMR)
Appearance: White to off-white solid
Identity: 1H-NMR

Properties

Solvents: Soluble in chloroform.
Melting Point: 127-132° C
Optical Activity: α20/D -32°±2°, c = 1.7 in methanol
Refractive Index: n20D = 1.56
Density: 1.27 g/cm3

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.

Hazard statements: H315-H319-H335
Precautionary statements: P261-P305+P351+P338
GHS Symbol: GHS07
Signal word: Warning

Description: N-Z-L-Homoserine lactone is a synthetic building block or intermediate used in the synthesis of biological active agents and analogs of bacterial quorum-sensing signaling molecules. N-Z-L-Homoserine lactone is shown to irreversibly inactivate the 3C cysteine proteinase of hepatitis A virus (HAV) and might be a scaffold for potent cyteine protein inhibtiors. Shown to reduce the lag phase duration (LPD) and increase the exponential growth rate (EGR) of three strains of Pseudomonas fluorescens isolated from refrigerated raw milk.
Smiles: O=C1OCC[C@@H]1NC(OCC2=CC=CC=C2)=O
InChi Key: FKWDZIFOVOUDAG-JTQLQIEISA-N
References: [1] M. Seki & K. Matsumoto, et al., Tetrahedr. Lett. 37, 3165 (1996) , [2] M.S. Lall, et al., Org. Lett. 1, 803 (1999) , [3] N. Fotouhi, et al., Bioorg. Med. Chem. Lett. 10, 1167 (2000) , [4] M.S. Lall, et al., J. Org. Chem. 67, 1536 (2002) , [5] G. Dunstall, et al., J. Dairy Res. 72, 276 (2005) , [6] D. Shetty, at al., Nucl. Med. Biol. 37, 893 (2010) , [7] S.P. Singh, et al., J. Org. Chem. 76, 6825 (2011) , [8] Z. Cui, et al., Food Chem. 328, 127063 (2020)
InChi: InChI=1S/C12H13NO4/c14-11-10(6-7-16-11)13-12(15)17-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,13,15)/t10-/m0/s1

N-Z-L-Homoserine lactone is a synthetic building block or intermediate used in the synthesis of biological active agents and analogs of bacterial quorum-sensing signaling molecules. N-Z-L-Homoserine lactone is shown to irreversibly inactivate the 3C cysteine proteinase of hepatitis A virus (HAV) and might be a scaffold for potent cyteine protein inhibtiors. Shown to reduce the lag phase duration (LPD) and increase the exponential growth rate (EGR) of three strains of Pseudomonas fluorescens isolated from refrigerated raw milk.

SKU: H0379 Category: Building Blocks, Intermediates, Reagents

Additional information

Additional information

Synonyms	N-Benzyloxycarbonyl-L-homoserine Lactone, N-Cbz-L-Homoserine lactone, N-Carbobenzoxy-L-homoserine Lactone, (S)-&alpha,-(Cbz-amino)-&gamma,-butyrolactone
Purity	≥95% (NMR)
Appearance	White to off-white solid
CAS-Number	35677-89-5
Molecular Formula	C12H13NO4
Molecular Weight	235.24
Identity	1H-NMR
Solvents	Soluble in chloroform.
Melting Point	127-132° C
Optical Activity	α20/D -32°±2°, c = 1.7 in methanol
Refractive Index	n20D = 1.56
Density	1.27 g/cm3
Smiles	O=C1OCC[C@@H]1NC(OCC2=CC=CC=C2)=O
InChi Key	FKWDZIFOVOUDAG-JTQLQIEISA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Hazard statements	H315-H319-H335
Precautionary statements	P261-P305+P351+P338
GHS Symbol	GHS07
Signal word	Warning
References	[1] M. Seki & K. Matsumoto, et al., Tetrahedr. Lett. 37, 3165 (1996), [2] M.S. Lall, et al., Org. Lett. 1, 803 (1999), [3] N. Fotouhi, et al., Bioorg. Med. Chem. Lett. 10, 1167 (2000), [4] M.S. Lall, et al., J. Org. Chem. 67, 1536 (2002), [5] G. Dunstall, et al., J. Dairy Res. 72, 276 (2005), [6] D. Shetty, at al., Nucl. Med. Biol. 37, 893 (2010), [7] S.P. Singh, et al., J. Org. Chem. 76, 6825 (2011), [8] Z. Cui, et al., Food Chem. 328, 127063 (2020)
InChi	InChI=1S/C12H13NO4/c14-11-10(6-7-16-11)13-12(15)17-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,13,15)/t10-/m0/s1
Quantity	100 mg, 250 mg, 1 g, Bulk