146346-82-9

Basic information

• Product Name: FMOC-THR(TBDMS)-OH
• Synonyms: FMOC-L-THR(TBDMS)-OH;FMOC-THR(TBDMS)-OH;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-O-(TERT-BUTYL-DIMETHYLSILYL)-L-THREONINE;fmoc-o-(tert.-butyldimethylsilyl)-l-threonine;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-O-(T-BUTYL-DIMETHYLSILYL)-L-THREONINE;N-ALPHA-(9-FLUOROENYLMETHYLOXYCARBONYL)-O-(T-BUTYL-DIMETHYLSILYL)-L-THREONINE;O-[(1,1-Dimethylethyl)dimethylsilyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine;(9H-Fluoren-9-yl)MethOxy]Carbonyl Thr(TBDMS)-OH
• CAS NO: 146346-82-9
• Molecular Formula: C₂₅H₃₃NO₅Si
• Molecular Weight: 455.62
• Product Categories: Amino Acids
• Mol File: 146346-82-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 577.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.136±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.38±0.10(Predicted)
• BRN: 5888824
• CAS DataBase Reference: FMOC-THR(TBDMS)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-THR(TBDMS)-OH(146346-82-9)
• EPA Substance Registry System: FMOC-THR(TBDMS)-OH(146346-82-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 146346-82-9(Hazardous Substances Data)

Usage

General Description

FMOC-THR(TBDMS)-OH is a chemical compound composed of FMOC, THR, and TBDMS functional groups. FMOC, or 9-fluorenylmethoxycarbonyl, is commonly used as a protective group for amino acids. THR refers to threonine, an essential amino acid that plays a key role in protein synthesis and various biochemical processes in the body. TBDMS, or tert-butyldimethylsilyl, is a protective group commonly used in organic synthesis, particularly in the protection of alcohols and amines. When combined, FMOC-THR(TBDMS)-OH can be used in peptide synthesis and solid-phase peptide synthesis, as well as in various organic chemistry applications. FMOC-THR(TBDMS)-OH is often used to protect the threonine amino acid while allowing for selective manipulation of other functional groups.

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 104197-64-0 O-(tert-butyldimethylsilyloxy)-L-threonine 
• 73731-37-0 Fmoc-Thr-OH 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 71989-35-0 Fmoc-Thr(tBu)-OH 

Downstream Products

• 915098-73-6 C₆₄H₉₃N₁₁O₂₈P₂Si₂ 
• 915098-66-7 Alloc-Gly-Ala-Tyr-Thr(TBS)-Gly-OH 
• 1240360-55-7 Z-Phe-Ala-Thr(TBS)-Met-Arg(Tos)-Tyr(Pen)-Pro-Ser(tBu)-Asp(OAll)-Ser(Bzl)-Asp(OtBu)-OH 

Relevant articles and documents

Synthesis of autophagosomal marker protein LC3-II under detergent-free conditions

Just add oil: A new detergent-free method was developed to synthesize lipidated proteins using a light-activatable solubilizing side chain (in dashed circle, see scheme) to assist the ligation of the lipopeptides. This method allows the efficient preparation of a phosphatidylethanolamine-conjugated autophagosomal marker protein (LC3-II) as well as labeled derivatives of LC3-II, which can be used to study autophagy regulation. Copyright

Synthesis of N-protected N-methyl serine and threonine

Two efficient and convenient syntheses of N-Cbz and N-Fmoc N-methyl serine and threonine are described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone.

Application of t-Butyldimethylsilyl Ethers of Serine, Threonine and Tyrosine in Peptide Synthesis

The utility of Tbdms (t-butyldimethylsilyl) ethers, prepared conveniently in a one pot procedure from Nα-Fmoc (9-fluorenylmethoxycarbonyl) and Nα-Z (benzyloxycarbonyl) hydroxyamino acids, is demonstrated: peptide bond formation and esterification to 4-alkoxybenzylalcohol resin are achieved readily with these derivatives.The lability of the Tbdms ethers to various reagents enables selective deprotection of the hydroxyl side-chains assembly, desirable, e.g., for phosphorylation of glycosylation.