H-D-Thr-OBzl · oxalate (1:1) is a protected, isotopically unlabelled amino acid derivative featuring a D-threonine backbone bearing a benzyl ester at the carboxyl terminus (Thr-OBzl) and a free amino group in the form of an N-terminus hydrogen (H-D-). The molecule is present as a 1:1 oxalate salt, pairing the amino functionality with oxalate while retaining the threonine side chain hydroxyl as a polar, hydrogen-bonding group that can influence reactivity and solubility. In peptide and amino acid synthesis workflows, this benzyl-protected ester form serves as a carboxyl-protected intermediate that can be handled for stepwise assembly or for preparing further threonine-containing derivatives, while the salt form supports controlled physical handling and analytical characterization of the amino acid ester.
CAT No: CP26699
CAS No:201274-09-1
Synonyms/Alias:201274-09-1;D-THREONINE-OBZLOXALATE;H-D-Thr-OBzl.oxalate(1:1)
H-D-Thr-OBzl · oxalate (1:1) is a chiral, N-protected threonine benzyl ester salt in which the amino functionality is blocked as a benzyloxycarbonyl (carbamate) derivative while the carboxyl group is masked as a benzyl ester. The D-configuration at the threonine stereocenter and the side-chain hydroxyl group provide defined stereochemical recognition and a handle for selective functional group transformation. The benzyl ester and carbamate protection pattern supports peptide coupling compatibility by enabling controlled deprotection under hydrogenolysis or orthogonal conditions, while the oxalate counterion can influence crystallization behavior and handling in synthesis. The compound therefore functions as a chiral amino acid intermediate and peptide building block precursor for assembling stereochemically defined threonine-containing sequences and for downstream derivatization of the side-chain hydroxyl.
1. Peptide Synthesis
H-D-Thr-OBzl · oxalate (1:1) is used in peptide synthesis workflows requiring a D-threonine residue with orthogonally protected functionality. The N-protected carbamate and C-terminal benzyl ester protect the amino and carboxyl groups during coupling, while the side-chain hydroxyl remains available for controlled protection or selective modification. The benzyl ester can be removed by hydrogenolysis to reveal a free carboxyl for subsequent chain extension or to generate a defined C-terminus for fragment ligation. Incorporation of the D-stereocenter supports stereochemically constrained peptide analog construction and can be applied to generate peptide libraries for mechanistic studies of stereochemical effects on backbone recognition. The oxalate salt form can also support reproducible weighing and intermediate preparation in synthetic sequences that rely on stable, isolable protected amino acid forms.
2. Side-Chain Functionalization
H-D-Thr-OBzl · oxalate (1:1) supports amino acid derivatization strategies targeting the threonine side-chain hydroxyl for chemical biology and materials-oriented synthesis. The side-chain alcohol can be converted into protected hydroxyl derivatives or activated intermediates, enabling formation of O-linked substituents such as ethers or ester-linked handles for later conjugation steps. The preserved stereochemistry at the D-threonine center helps maintain spatial orientation of the side-chain substituent when building peptidomimetics or functionalized oligoamides. The benzyl ester and N-protection reduce undesired reactions during hydroxyl functional group transformations, allowing sequential chemoselective steps that culminate in a defined functional amino acid or peptide fragment. Downstream utility includes preparing stereodefined intermediates for affinity probes, crosslinkable reagents, and structured scaffolds used in applied synthetic organic chemistry.
3. Protected Amino Acid Chemistry
H-D-Thr-OBzl · oxalate (1:1) functions as a chiral protected amino acid intermediate for controlled N- and C-terminal manipulation in fine chemical synthesis. The carbamate-type N-protection and benzyl ester C-protection provide a predictable protection/deprotection logic that can be matched to peptide coupling reagents and orthogonal protecting-group schemes for neighboring residues. The D-configuration enables stereoselective incorporation into unnatural or stereochemically enriched peptide constructs, supporting studies that distinguish D-amino acid effects on conformational preferences and chemical stability. The oxalate counterion can be leveraged in process design to obtain a handleable solid form for intermediate preparation and for consistent downstream conversion to activated coupling derivatives. The compound's protection pattern also makes it suitable for manufacturing route planning where hydrogenolysis-compatible protecting groups are required to unlock reactive termini without disturbing side-chain functionalization plans.
4. Peptidomimetics And SAR Studies
H-D-Thr-OBzl · oxalate (1:1) is applicable to peptidomimetic construction and structure-activity relationship studies that require threonine analogs with defined stereochemical identity. The threonine backbone features a side-chain hydroxyl that can be retained, protected, or transformed into bioisosteres, while the protected N- and C-termini facilitate assembly into amide-rich scaffolds. D-threonine incorporation can be used to generate stereochemically constrained analog series for evaluating how inversion at the chiral center affects binding-site complementarity and metabolic stability proxies in SAR workflows. The benzyl ester and carbamate protection enable stepwise synthesis of analogs with controlled termini for fragment coupling, cyclization, or conjugation to carrier molecules. The resulting D-threonine-containing building blocks integrate into broader amino acid chemistry programs aimed at generating chemically defined libraries for mechanistic and recognition studies.
5. Pharmaceutical Intermediate Preparation
H-D-Thr-OBzl · oxalate (1:1) serves as a process-relevant intermediate in the manufacture of stereochemically defined peptide fragments and amino acid-derived intermediates used in pharmaceutical-grade synthetic programs. The compound's protected amino and carboxyl functionalities align with industrial peptide coupling practices, where orthogonal protection reduces side reactions and supports reproducible conversion to activated derivatives for chain assembly. The benzyl ester protection is compatible with hydrogenolysis steps commonly integrated into manufacturing sequences to reveal carboxylic acid termini without introducing additional functional group complexity. The D-threonine stereocenter provides a controlled chiral element that can be carried through to downstream drug-like peptide analogs or peptidomimetic candidates during synthetic scale-up. The oxalate salt form can also support stable intermediate handling and crystallization-oriented processing for amino acid derivative production.
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