Boc-Leu-OSu

Boc-Leu-OSu is a Boc-protected leucine N-hydroxysuccinimide ester, featuring the leucine side chain and an activated carboxyl group converted to an OSu (N-hydroxysuccinimide) ester for amide bond formation. The molecule contains a tert-butoxycarbonyl (Boc) protecting group on the amino functionality while the OSu ester masks the carboxyl group as a leaving-group-bearing electrophile, and it is typically handled as a reactive peptide-coupling intermediate rather than a free amino acid. Boc-Leu-OSu is used in solution-phase or solid-phase peptide synthesis and in chemical conjugation workflows where controlled coupling of the leucine residue to amines is required, including preparation of leucine-containing peptide derivatives and amide-linked biomolecule conjugates.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP27020

CAS No:3392/9/4

Synonyms/Alias:Boc-Leu-OSu;3392-09-4;Boc-L-leucinehydroxysuccinimideester;Boc-L-LeucineN-hydroxysuccinimideester;N-(tert-Butoxycarbonyl)-L-leucineN-hydroxysuccinimideester;AmbotzBAA5770;N-Boc-Leu-(Succinimidyl)OH;15454_ALDRICH;SCHEMBL3752138;15454_FLUKA;MolPort-003-926-804;ZINC1576298;4017AB;CB-344;AKOS016003058;AM81885;AK-81129;HE062331;KB-48345;ST2412707;K-0046;TERT-BUTYL(S)-[1-[[(25-DIOXO-1-PYRROLIDINYL)OXY]CARBONYL]-3-METHYLBUTYL]CARBAMATE

Chemical Name:N-alpha-t-Butyloxycarbonyl-L-leucine succinimidyl ester

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M.F/Formula
C15H24N2O6
M.W/Mr.
328.37

Boc-Leu-OSu is a Boc-protected leucine N-hydroxysuccinimide ester (OSu), engineered for efficient coupling in peptide and amide bond formation workflows. As an activated amino acid derivative, it provides a pre-activated carboxylate that is commonly used by peptide chemists to minimize coupling variability during segment assembly and rapid synthesis. The Boc group supports controlled N-protection for downstream peptide elongation, while the OSu leaving group is designed to promote reactivity toward nucleophiles such as amines under standard peptide chemistry conditions.

1. Segment Coupling Reagent

Boc-Leu-OSu is frequently used in peptide synthesis for coupling leucine-containing segments where an activated carboxylate is preferred over less reactive acid forms. Peptide chemistry groups developing protected peptide fragments, including those assembling longer sequences by fragment condensation, rely on OSu activation to improve consistency of amide bond formation at the leucine position. The Boc protection on the amino nitrogen helps maintain orthogonal control of the N-terminus throughout assembly, supporting workflows that require a defined protection pattern for subsequent deprotection and chain extension.

2. Solution-Phase Peptide Assembly

Boc-Leu-OSu is used in solution-phase peptide synthesis to support stepwise construction of protected peptide intermediates and custom peptide libraries. Researchers performing solution-phase couplings often choose OSu esters to streamline the activation step and reduce dependence on in situ coupling reagent performance across different substrates. In these workflows, Boc-Leu-OSu functions as a leucine building block that can be coupled to appropriately protected amines, enabling controlled generation of amide-linked intermediates that are carried forward to further elongation or final deprotection.

3. Protected Peptide Intermediate Development

Boc-Leu-OSu is well suited to the preparation of leucine-containing protected peptide intermediates used in medicinal chemistry and process chemistry development. Pharmaceutical intermediate teams and peptide manufacturing laboratories commonly use activated amino acid derivatives to standardize intermediate quality during the synthesis of key building blocks for larger targets. The combination of Boc N-protection and OSu activation supports reliable incorporation of leucine into amide-linked structures while preserving the protection state required for downstream transformations, purification, and scale-up-oriented synthetic planning.

4. Amide Bond Formation Studies

Boc-Leu-OSu is also applied in chemical synthesis contexts where a Boc-protected amino acid OSu ester serves as a practical activated carboxylate for forming amide bonds with amine nucleophiles. Chemical biology and synthetic chemistry teams may use it to generate defined leucine-containing amide products as part of probe, linker, or peptide-analog intermediate preparation. Because the OSu ester is designed for coupling efficiency, it is often selected when reproducible amide formation is needed to support iterative structure-building or library synthesis rather than relying on less activated carboxylic acid derivatives.

Size
5 g;25 g;100 g;
Abbr
Boc-Leu-OSu
InChI
1S/C15H24N2O6/c1-9(2)8-10(16-14(21)22-15(3,4)5)13(20)23-17-11(18)6-7-12(17)19/h9-10H,6-8H2,1-5H3,(H,16,21)/t10-/m0/s1
InChI Key
WXRGJQZMGGGTSS-JTQLQIEISA-N
Canonical SMILES
CC(C)CC(C(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C

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