18783-53-4

Basic information

• Product Name: H-D-SER(TBU)-OH
• Synonyms: O-T-BUTYL-D-SERINE;H-D-SER(BUT)-OH;H-D-SER(TBU)-OH;D-SERINE(TBU)-OH;O-TERT-BUTYL-D-SERINE;tert-butylserine;(2S)-2-(tert-butylaMino)-3-hydroxypropanoic acid;O-(1,1-Dimethylethyl)-D-serine
• CAS NO: 18783-53-4
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.2
• Product Categories: Amino Acid Derivatives;Amino Acids
• Mol File: 18783-53-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 266 °C at 760 mmHg
• Flash Point: 114.6 °C
• Appearance: /
• Density: 1.08 g/cm³
• Vapor Pressure: 0.00257mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: 2-8°C
• CAS DataBase Reference: H-D-SER(TBU)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-D-SER(TBU)-OH(18783-53-4)
• EPA Substance Registry System: H-D-SER(TBU)-OH(18783-53-4)

Safety Data

• Hazardous Substances Data: 18783-53-4(Hazardous Substances Data)

Usage

General Description

H-D-SER(TBU)-OH is the chemical structure of N-tert-butoxycarbonyl-L-serine, a derivative of L-serine, which is a non-essential amino acid. H-D-SER(TBU)-OH is commonly used in the synthesis of peptides and pharmaceuticals. It serves as a building block for peptide synthesis and can be used as a protecting group for serine residues during peptide assembly. The tert-butoxycarbonyl (TBU) group is often added to protect the serine residue from unwanted reactions during peptide synthesis and can be removed later in the process. Overall, H-D-SER(TBU)-OH plays a crucial role in the production of various peptide-based compounds and pharmaceuticals.

InChI:InChI=1/C7H15NO3/c1-7(2,3)11-4-5(8)6(9)10/h5H,4,8H2,1-3H3,(H,9,10)/t5-/m1/s1

Upstream product

• 18822-58-7 (S)-O-tert-butylserine 

Downstream Products

• 1025982-20-0 (R)-3-tert-Butoxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid 
• 1026585-04-5 (R)-3-tert-Butoxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid tert-butyl ester 
• 1026241-96-2 (R)-2-[Benzyl-(4-methoxy-benzenesulfonyl)-amino]-3-tert-butoxy-propionic acid 
• 1026007-37-3 (R)-2-[Benzyl-(4-methoxy-benzenesulfonyl)-amino]-3,N-di-tert-butoxy-propionamide 
• 248921-66-6 (2R)-3-(tert-butoxy)-2-(tert-butoxycarbonylamino)-propanoic acid 
• 928211-73-8 (4-chlorobenzylsulfonyl)-D-Ser(O-tBu)-Cl 
• 928211-72-7 (4-chlorobenzylsulfonyl)-D-Ser(O-tBu)-OH 
• 928211-75-0 (4-chlorobenzylsulfonyl)-D-Ser(O-tBu)-N-Me-Ala-4-nitro-benzylamide 

Relevant articles and documents

Effect of the Side Chain on the Racemization of Amino Acids in Aqueous Solution

The rate of racemization of 13 amino acids possessing hydroxy, carboxy, alkoxy, carboalkoxy, alkyl, aryl, and thioether side chains were compared.Reaction conditions were identical for all amino acids studied.Gas chromatography was used to determine the percent of D isomer present.Hydroxy amino acids racemized most rapidly, but conversion to an ether function reduced the rate considerably.The increased racemization rate of methionine (R = CH2CH2SCH3) over Ala (R = CH3) has been attributed to orbital overlap from the sulfur.Asp racemized faster than Glu, α-aminoadipic acid, and pyroglutamic acid. β- and γ-monomethyl esters of aspartic and glutamic acids, respectively, racemized only slightly faster than the corresponding free acids.The slight increase in rate appears attributable to a solvent change brought on by ester hydrolysis.Under the reaction conditions, pH 8 and 140 deg C, hydrolysis of the esters competed favorably with racemization at the methine carbon.The relatively lower racemization rate observed in the case of Glu compared with Asp resulted from the slow formation of pyroglutamic acid.Pyroglutamic acid racemized at a considerably slower rate than acidic amino acids.The differences in the racemization rates with changes in the R group are discussed in terms of several factors, including intramolecular reactions, direct field effects, orbital overlap, and solvation effects, as well as inductive, resonance, and steric factors.