73724-48-8

Basic information

• Product Name: FMOC-THR(BZL)-OH
• Synonyms: FMOC-L-THR(BZL)-OH;FMOC-THREONINE(BZL)-OH;N-ALPHA-FMOC-O-BENZYL-L-THREONINE;N-A-FMOC-O-BENZYL-L-THREONINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-O-BENZYL-L-THREONINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-O-BENZYL-L-THREONINE;N-ALPHA-(9-FLUOROENYLMETHYLOXYCARBONYL)-O-BENZYL-L-THREONINE;Fmoc-L-Thr-OBzl
• CAS NO: 73724-48-8
• Molecular Formula: C₂₆H₂₅NO₅
• Molecular Weight: 431.48
• Product Categories: Amino Acids
• Mol File: 73724-48-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 656.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.257±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 10.34±0.46(Predicted)
• CAS DataBase Reference: FMOC-THR(BZL)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-THR(BZL)-OH(73724-48-8)
• EPA Substance Registry System: FMOC-THR(BZL)-OH(73724-48-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 73724-48-8(Hazardous Substances Data)

Usage

General Description

FMOC-THR(BZL)-OH is a chemical compound that consists of a FMOC (9-fluorenylmethyloxycarbonyl) protecting group, a THR (threonine) amino acid residue and a BZL (benzyl) ester group. The FMOC protecting group is commonly used in peptide synthesis to protect the N-terminal amino group and can be easily removed with a base. The THR amino acid is a polar, hydrophilic amino acid with a hydroxyl group in its side chain. The BZL ester group is commonly used for introducing a carboxyl group in peptide chemistry. FMOC-THR(BZL)-OH is therefore a versatile compound that can be used in the synthesis of peptides and other organic molecules in the field of biochemistry and pharmaceuticals.

Upstream product

• 100-39-0 benzyl bromide 
• 73731-37-0 Fmoc-Thr-OH 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 86088-59-7 L-threonine benzyl ester hemioxalate 
• 86088-58-6 ((9-fluorenylmethyl)oxy)carbonyl chloroformate 
• 201274-07-9 L-threonine benzyl ester oxalate salt 

Downstream Products

• 134354-93-1 N-(9-Fluorenylmethoxycarbonyl)-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-(1-4)-O-(3,6-di-O-acetyl-2-desoxy-2-iod-α-D-mannopyranosyl)-L-threonin-benzylester 
• 134262-40-1 N-(9-Fluorenylmethoxycarbonyl)-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-O-(3,6-di-O-acetyl-2-desoxy-2-iod-α-D-mannopyranosyl)-L-threonin-benzylester 
• 134262-40-1 (2S,3R)-3-[(2R,3R,4S,5R,6R)-4-Acetoxy-6-acetoxymethyl-3-iodo-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester 
• 148806-97-7 N^α-fluoren-9-ylmethoxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-threonine benzyl ester 
• 191849-79-3 N^α-fluoren-9-ylmethoxycarbonyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-threonine benzyl ester 
• 196313-91-4 N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-threonine benzylester 
• 100938-55-4 N-(9H-fluorene-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester 
• 1353655-04-5 C₃₅H₄₅NO₅Si 
• 1353655-02-3 N-Fmoc-O-benzyl-L-threonine benzyl ester 
• 1353654-79-1 (S)-4-(benzyloxy)-5-((R)-1-(methoxy)ethyl)-1H-pyrrol-2(5H)-one 
• 1353654-86-0 (5Z)-4-(benzyloxy)-5-ethylidene-1H-pyrrol-2(5H)-one 
• 1353654-65-5 (2S,3R)-benzyl 2-amino-3-((triisopropylsilyl)oxy)butanoate 
• 1353654-66-6 (2S,3R)-benzyl 2-methylamino-3-((triisopropylsilyl)oxy)butanoate 
• 1353655-05-6 (2S,3R)-benzyl 2-(2-nitrobenzenesulfonyl)amino-3-((triisopropylsilyl)oxy)butanoate 

Relevant articles and documents

Use of remote acyl groups for stereoselective 1,2-: Cis -glycosylation with fluorinated glucosazide thiodonors

Fluorinated glycans are valuable probes for studying carbohydrate-protein interactions at the atomic level. Glucosamine is a ubiquitous component of glycans, and the stereoselective synthesis of α-linked fluorinated glucosamine is a challenge associated with the chemical synthesis of fluorinated glycans. We found that introducing a 6-O-acyl protecting group onto 3-fluoro and 4-fluoro glucosazide thiodonors endowed them with moderate α-selectivity in the glycosylation of carbohydrate acceptors, which was further improved by adjusting the acceptor reactivity via O-benzoylation. Excellent stereoselectivity was achieved for 3,6-di-O-acyl-4-fluoro analogues. The glycosylation of threonine-derived acceptors enabled the stereoselective synthesis of the protected fluorinated analogue of α-GlcNAc-O-Thr, a moiety abundant in cell-surface O-glycans of the protozoan parasite Trypanosoma cruzi. DFT calculations supported the involvement of transient cationic species which resulted from the stabilization of the oxocarbenium ion through O-6 acyl group participation. This journal is

α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi

This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(αGalNAc)Ser] 3 and cyclo[Asp-(αGalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids αGalNAc-Ser 7 or αGalNAc-Thr 8 and the amino acid (O-tBu)-Asp 17, followed by one-pot deprotection-cyclisation reaction in the presence of 20% piperidine in DMF. The protected glycosyl amino acid intermediates 7 and 8 were, in turn, obtained by α-selective, HgBr2-catalysed glycosylation reactions of Fmoc-Ser/Thr benzyl esters 12/14 with αGalN3Cl 11, being, subsequently, fully deprotected for comparative biological assays. The DKPs 3 and 4 showed relevant anti-trypanosomal effects (IC50 282-124 μM), whereas glycosyl amino acids 1 and 2 showed better TcTS inhibition (57-79%) than the corresponding DKPs (13-25%).

Design, synthesis and the effect of 1,2,3-triazole sialylmimetic neoglycoconjugates on Trypanosoma cruzi and its cell surface trans-sialidase

This work describes the synthesis of a series of sialylmimetic neoglycoconjugates represented by 1,4-disubstituted 1,2,3-triazole-sialic acid derivatives containing galactose modified at either C-1 or C-6 positions, glucose or gulose at C-3 position, and by the amino acid derivative 1,2,3-triazole fused threonine-3-O-galactose as potential TcTS inhibitors and anti-trypanosomal agents. This series was obtained by Cu(I)-catalysed azide-alkyne cycloaddition reaction ('click chemistry') between the azido-functionalized sugars 1-N3-Gal (commercial), 6-N 3-Gal, 3-N3-Glc and 3-N3-Gul with the corresponding alkyne-based 2-propynyl-sialic acid, as well as by click chemistry reaction between the amino acid N3-ThrOBn with 3-O-propynyl-GalOMe. The 1,2,3-triazole linked sialic acid-6-O-galactose and the sialic acid-galactopyranoside showed high Trypanosoma cruzi trans-sialidase (TcTS) inhibitory activity at 1.0 mM (approx. 90%), whilst only the former displayed relevant trypanocidal activity (IC50 260 μM). These results highlight the 1,2,3-triazole linked sialic acid-6-O-galactose as a prototype for further design of new neoglycoconjugates against Chagas' disease.