1676-81-9

Basic information

• Product Name: N-Cbz-L-serine methyl ester
• Synonyms: N-CARBOBENZOXY-L-SERINE METHYL ESTER;N-CARBOBENZYLOXY-L-SERINE METHYL ESTER;N-CBZ-L-SERINE METHYL ESTER;N-ALPHA-CARBOBENZOXY-L-SERINE METHYL ESTER;n-z-l-serine methyl ester;Z-SER-OME;Z-SERINE-OME;Z-L-SERINE METHYL ESTER
• CAS NO: 1676-81-9
• Molecular Formula: C₁₂H₁₅NO₅
• Molecular Weight: 253.25
• EINECS: 1533716-785-6
• Product Categories: Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Amino Acid Derivatives;Peptide Synthesis;Serine
• Mol File: 1676-81-9.mol

Chemical Properties

• Melting Point: 41-43 °C(lit.)
• Boiling Point: 170 °C0.01 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Pale yellow/Viscous Liquid or Solid
• Density: 1.2499 (rough estimate)
• Vapor Pressure: 1.3E-08mmHg at 25°C
• Refractive Index: -15 ° (C=1, MeOH)
• Storage Temp.: -15°C
• Solubility: Chloroform, Methanol
• PKA: 10.49±0.46(Predicted)
• CAS DataBase Reference: N-Cbz-L-serine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-L-serine methyl ester(1676-81-9)
• EPA Substance Registry System: N-Cbz-L-serine methyl ester(1676-81-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 1676-81-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Cbz-L-serine methyl ester is used as an inhibitor for Mycobacterium tuberculosis in various studies. It plays a crucial role in understanding the mechanisms of tuberculosis and contributes to the development of potential treatments against this bacterial infection.
Used in Obesity Treatment Research:
N-Cbz-L-serine methyl ester is used as a key intermediate in the synthesis of pyrazinecarboxamide-based compounds, which act as inhibitors of diacylglycerol acetyltransferases (DGAT). These inhibitors are being investigated for their potential to treat obesity by regulating lipid metabolism and reducing fat accumulation in the body.
Used in Chemical Synthesis:
As a versatile chemical building block, N-Cbz-L-serine methyl ester is employed in the synthesis of various complex organic molecules and pharmaceutical compounds. Its unique structure allows for further functionalization and modification, making it a valuable asset in the development of new drugs and chemicals.

InChI:InChI=1/C12H15NO5/c1-17-11(15)10(7-14)13-12(16)18-8-9-5-3-2-4-6-9/h2-6,10,14H,7-8H2,1H3,(H,13,16)/t10-/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 2788-84-3 (S)-serine methyl ester 
• 501-53-1 benzyl chloroformate 
• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 
• 67-56-1 methanol 
• 108655-52-3 1-benzyloxycarbonyl-v-triazolo<4,5-b>pyridine 
• 56-45-1 L-serin 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 1258782-80-7 C₁₄H₁₇NO₆ 
• 173947-21-2 N-benzyloxycarbonyl-N-methyl-L-serine 
• 1671-87-0 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine 
• 1067639-65-9 O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-N[(phenylmethoxy)carbonyl]-L-serine methyl ester 

Downstream Products

• 26582-86-5 benzyl (1S)-2-hydrazino-1-(hydroxymethyl)-2-oxoethylcarbamate 
• 1872-59-9 (S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoate 
• 158975-47-4 N-(carbobenzoxy)-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1<*>3)-L-serine methyl ester 
• 131919-40-9 C₄₆H₄₁NO₁₄ 
• 74084-36-9 3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester 
• 77870-91-8 (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propanoate 
• 77870-90-7 (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propanoate 
• 126686-65-5 Z-Ser-(Boc-Phe)-OMe 
• 77870-93-0 ester methylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-serine 
• 77870-92-9 ester methylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-serine 
• 142822-20-6 N-benzyloxycarbonyl-L-seryl-L-tyrosine tert-butyl ester 
• 153947-45-6 O-(3,4,6-Tri-O-benzyl-β-D-glucopyranosyl)-N-Cbz-L-serine methyl ester 
• 141662-73-9 o-(3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino-β-D-lyxo-hexopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester 
• 141662-74-0 O-(3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino-α-D-lyxo-hexopyranosyl)-N-benzyloxycarbonyl-L-serine methyl ester 

Relevant articles and documents

Synthesis and in vitro activity towards Mycobacterium tuberculosis of L-serinyl ester and amino derivatives of pyrazinoic acid

Reactions between either L-serine methyl ester hydrochloride (1), or the cbz derivative, methyl (S)-(+)-2-(benzyloxycarbonylamino)-3-hydroxypropanoate (2), and pyrazinoyl chloride (3), have been studied. Methyl (S)-(+)-2- benzyloxycarbonylamino-3-[(pyrazinecarbonyl)oxy]propionate (4), methyl (S)-(+)-3-hydroxy-2-[(pyrazine-2-carbonyl) aminolpropionoate (7), methyl 2-[(pyrazinecarbonyl)amino]acrylate (8) were obtained. Additional products, methyl (S)-(+)-2-benzyloxycarbonylamino-3-formyloxypropionoate (5) and methyl (R)-(+)-2-benzyloxycarbonylamino-3-chloropropionoate (6), were isolated from reaction of 2 with 3, in the presence of DMF remaining from the preparation of 3, from pyrazinecarboxylic acid. The coupling of pyrazinecarboxylic acid with 1, in the presence of DCC was prevented by the formation of the unreactive adduct between DCC and pyrazinoic acid. The compounds were tested against M. tuberculosis: compounds (8) and (6) exhibited a MIC (μg/ml) value of 50 and 100, respectively, compared to the MIC value of 100 for the first line TB drug, pyrazinamide. The confirmation of the structure of (8) was obtained via X-ray crystallography.

Glycosylated tris-bipyridine ferrous complexes as molecular mimics of densely packed glycoclusters on cell surfaces: spatial carbohydrate packing of glycoclusters changes on additions of salts

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On the mechanism of oxazoline-directed metalations: Evidence for nitrogen-directed reactions

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An efficient, stereocontrolled and versatile synthetic route to bicyclic partially saturated privileged scaffolds

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TOLL-LIKE RECEPTOR LIGANDS

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The first total synthesis of the potent anti-mycobacterial cyclic depsipeptide natural product ecumicin is described. Synthesis was achieved via a solid-phase strategy, incorporating the synthetic non-proteinogenic amino acids N-methyl-4-methoxy-l-tryptophan and threo-β-hydroxy-l-phenylalanine into the growing linear peptide chain. The synthesis employed key on-resin esterification and dimethylation steps as well as a final macrolactamization between the unusual N-methyl-4-methoxy-l-tryptophan unit and a bulky N-methyl-l-valine residue. The synthetic natural product possessed potent antimycobacterial activity against the virulent H37Rv strain of Mycobacterium tuberculosis (MIC90 = 312 nM).

Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate

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