Boc-Arg(Z)2-OSu

Boc-Arg(Z)2-OSu is a protected arginine-derived amino acid derivative featuring a guanidinium side chain and an N-terminal Boc (tert-butoxycarbonyl) protecting group, with the arginine side chain bearing two Z-type (benzyloxycarbonyl) functionalities. The molecule also contains an activated N-hydroxysuccinimide ester (OSu) at the carboxylate position, while the protected guanidinium region is designed to control chemoselectivity during peptide coupling and to reduce undesired side reactions. In synthesis, this activated, protected arginine building block is used to support stepwise assembly of peptides and peptide-related intermediates, where the OSu ester form provides a carboxyl-activation handle and the protecting groups maintain the side-chain integrity for subsequent deprotection and coupling steps.

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

CAT No: CP27435

CAS No:76052-29-4

Synonyms/Alias:BOC-ARG(Z)2-OSU;76052-29-4;BOC-ARG2-OSU;C31H37N5O10;6273AH;KM1729;ZINC150338765

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cGMP Peptide
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M.F/Formula
C31H37N5O10
M.W/Mr.
639.66

Boc-Arg(Z)2-OSu is a protected arginine derivative designed for peptide coupling chemistry. The molecule combines an N-terminal Boc-protection with a side-chain protected arginine guanidino functionality, and it is delivered as an active ester (OSu), enabling efficient amide bond formation during peptide assembly. This reagent format is widely used in peptide intermediate synthesis where controlled coupling and minimized side reactions are important for building protected peptide segments.

1. Peptide Segment Coupling

Boc-Arg(Z)2-OSu is commonly used as an activated arginine building block for solution-phase peptide synthesis and segment condensation workflows. Peptide chemists select the OSu active ester format to promote formation of the arginine-containing amide linkage under standard coupling conditions, supporting reliable incorporation of a protected arginine residue into growing peptide chains. The Boc-protected amino functionality and the protected side-chain guanidino pattern help maintain compatibility with multi-step peptide assembly, where orthogonal deprotection and side-chain stability are critical for downstream processing.

2. Protected Arginine Intermediate Synthesis

Boc-Arg(Z)2-OSu serves as a practical intermediate for preparing arginine-containing peptide fragments used in custom peptide manufacturing and laboratory-scale peptide library construction. Researchers rely on this reagent when they need a defined, protected arginine unit that can be introduced into a larger protected peptide scaffold without exposing reactive guanidino chemistry prematurely. The active ester functionality streamlines conversion into the corresponding peptide bond within protected environments, making it a common choice for assembling longer sequences where maintaining protecting-group integrity across steps improves overall workflow robustness.

3. Peptide Library and SAR Workflows

Boc-Arg(Z)2-OSu is frequently used in parallel synthesis efforts for peptide libraries and structure-activity relationship (SAR) studies that require systematic variation of peptide composition while keeping side-chain protection consistent. Medicinal chemistry and chemical biology groups often incorporate protected arginine residues using activated amino acid derivatives to ensure that each library member is assembled from standardized building blocks. The reagent's protected arginine format supports reproducible coupling into multiple peptide analogs, helping teams generate comparable peptide intermediates for subsequent purification and characterization steps.

4. Scale-Up for Research-Grade Peptides

Boc-Arg(Z)2-OSu is also applied in scaled synthesis of arginine-containing peptide intermediates where process reliability and handling of a pre-activated amino acid derivative are advantageous. Industrial peptide intermediate development teams use active ester amino acid reagents to reduce variability associated with in situ activation and to fit established coupling schedules for producing protected peptide segments. This makes Boc-Arg(Z)2-OSu a useful option when the goal is consistent incorporation of a protected arginine residue into batch-manufactured peptide intermediates for downstream research supply.

Size
1 g;5 g;
InChI
1S/C31H37N5O10/c1-31(2,3)45-30(42)33-23(26(39)46-36-24(37)16-17-25(36)38)15-10-18-32-27(34-28(40)43-19-21-11-6-4-7-12-21)35-29(41)44-20-22-13-8-5-9-14-22/h4-9,11-14,23H,10,15-20H2,1-3H3,(H,33,42)(H2,32,34,35,40,41)/t23-/m0/s1
InChI Key
HAKDQDAGZLXYNM-QHCPKHFHSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCCN=C(NC(=O)OCC1=CC=CC=C1)NC(=O)OCC2=CC=CC=C2)C(=O)ON3C(=O)CCC3=O

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