136523-92-7

Basic information

• Product Name: N-Fmoc-L-threonine Allyl Ester
• Synonyms: N-Fmoc-L-threonine Allyl Ester;N-(9-FluorenylMethoxycarbonyl)threonine Allyl Ester;N-[(9H-Fluoren-9-ylMethoxy)carbonyl]-L-threonine 2-Propen-1-yl Ester
• CAS NO: 136523-92-7
• Molecular Formula: C₂₂H₂₃NO₅
• Molecular Weight: 381.42172
• Product Categories: Amino Acids & Derivatives;Aromatics;Chiral Reagents;Aromatics, Amino Acids & Derivatives, Chiral Reagents
• Mol File: 136523-92-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 597.238°C at 760 mmHg
• Flash Point: 314.999°C
• Appearance: /
• Density: 1.228g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: N-Fmoc-L-threonine Allyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Fmoc-L-threonine Allyl Ester(136523-92-7)
• EPA Substance Registry System: N-Fmoc-L-threonine Allyl Ester(136523-92-7)

Safety Data

• Hazardous Substances Data: 136523-92-7(Hazardous Substances Data)

Usage

Uses

Threonine derivative.

InChI:InChI=1/C22H23NO5/c1-3-12-27-21(25)20(14(2)24)23-22(26)28-13-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h3-11,14,19-20,24H,1,12-13H2,2H3,(H,23,26)/t14-,20+/m1/s1

Upstream product

• 106-95-6 allyl bromide 
• 612490-86-5 C₂₆H₃₁NO₅ 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 71989-35-0 Fmoc-Thr(tBu)-OH 
• 73731-37-0 Fmoc-Thr-OH 

Downstream Products

• 384346-81-0 N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester 
• 174783-86-9 N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine 
• 273944-57-3 N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester 
• 384346-83-2 N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine 
• 384346-82-1 N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester 
• 384346-84-3 N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine allyl ester 
• 384346-85-4 N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine allyl ester 
• 116783-35-8 N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine 
• 301843-65-2 N-(9H-fluoren-9-ylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester 

Relevant articles and documents

Activity and Predicted Nephrotoxicity of Synthetic Antibiotics Based on Polymyxin B

The polymyxin lipodecapeptides colistin and polymyxin B have become last resort therapies for infections caused by highly drug-resistant Gram-negative bacteria. Unfortunately, their utility is compromised by significant nephrotoxicity and polymyxin-resistant bacterial strains. We have conducted a systematic activity-toxicity investigation by varying eight of the nine polymyxin amino acid free side chains, preparing over 30 analogues using a novel solid-phase synthetic route. Compounds were tested against a panel of Gram-negative bacteria and counter-screened for in vitro cell toxicity. Promising compounds underwent additional testing against primary kidney cells isolated from human kidneys to better predict their nephrotoxic potential. Many of the new compounds possessed equal or better antimicrobial potency compared to polymyxin B, and some were less toxic than polymyxin B and colistin against mammalian HepG2 cells and human primary kidney cells. These initial structure-activity and structure-toxicity studies set the stage for further improvements to the polymyxin class of antibiotics.

METHOD OF PREPARING GLYCOPEPTIDES

A method is provided for the synthesis of glycopeptides using a sugar assisted ligation strategy, wherein an N-terminal peptide portion in the form of a thioester is coopled with a C-terminal peptide portion bearing a carbohydrate moiety comprising a thiol group.

Scalable synthesis of Fmoc-protected GalNAc-threonine amino acid and TN antigen via nickel catalysis

The highly α-selective and scalable synthesis of the Fmoc-protected GalNAc-threonine amino acid and TN antigen in gram scale (0.5-1 g) is described. The challenging 1,2-cis-2-amino glycosidic bond is addressed through a coupling of threonine residues with C(2)-N-ortho-(trifluoromethyl)benzylidenamino trihaloacetimidate donors mediated by Ni(4-F-PhCN)4(OTf)2. The desired 1,2-cis-2-amino glycoside was obtained in 66% yield (3.77 g) with α-only selectivity and subsequently transformed into the Fmoc-protected GalNAc-threonine and TN antigen. This operationally simple procedure no longer requires utilization of the commonly used C(2)-azido donors and overcomes many of the limitations associated with the synthesis of 1,2-cis linkage.