Rink Amide Linker

Rink Amide Linker is a solid-phase peptide synthesis linker that features a Rink amide core designed to generate a C-terminal peptide amide upon cleavage. The linker is typically assembled on a resin through a stable attachment point and incorporates a functional handle that allows stepwise coupling of protected amino acids, while the terminal amide-forming architecture controls the chemoselective release of the growing peptide chain. In peptide chemistry workflows, it is employed as a precursor for preparing C-terminally amidated peptide products for structure-activity studies, analytical standards, and the synthesis of peptide-related intermediates.

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

CAT No: CP26279

CAS No:126828-35-1

Synonyms/Alias:Fmoc-2,4-dimethoxy-4-(carboxymethyloxy)-benzhydrylamine;Rinkamidelinker;145069-56-3;4-[(2,4-Dimethoxyphenyl)(Fmoc-amino)methyl]phenoxyaceticacid;126828-35-1;2-(4-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)(2,4-dimethoxyphenyl)methyl)phenoxy)aceticacid;KnorrLinker;MFCD00153509;2-[4-[(2,4-dimethoxyphenyl)-(9H-fluoren-9-ylmethoxycarbonylamino)methyl]phenoxy]aceticAcid;4-[(2,4-Dimethoxyphenyl)[(9H-fluoren-9-ylmethoxy)carbonylamino]methyl]phenoxyaceticAcid;4-[(R,S)-a-[1-(9H-Fluoren-9-yl)-methoxy-formamido]-2,4-dimethoxybenzyl-phenoxyaceticacid;{4-[(2,4-DIMETHOXYPHENYL){[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO}METHYL]PHENOXY}ACETICACID;AmbotzRL-1027;PubChem12817;ACMC-20amr2;AC1MC4ZY;AC1Q48YV;38784_ALDRICH;SCHEMBL1745934;Jsp002638;38784_FLUKA;CTK0I3739;MolPort-003-876-280;CR-007;AKOS007930055;AM84412

Custom Peptide Synthesis
cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C32H29NO7
M.W/Mr.
539.59

Rink Amide Linker is a solid-supported peptide coupling linker designed for Fmoc-based solid-phase peptide synthesis, enabling C-terminal amide formation upon cleavage. The structure incorporates a polymerizable resin attachment point and a cleavable linker segment that translates the growing peptide chain to an amide at the C-terminus, with the resulting product retaining the stereochemical integrity of incorporated amino acids. The linker's chemistry is compatible with common orthogonal protection strategies used in peptide building blocks, including Fmoc removal under base and side-chain protecting-group stability during coupling cycles. Functional group behavior is governed by its cleavable bond and the amide-forming release mechanism, making it a practical intermediate platform for generating peptide libraries, peptide standards, and downstream synthetic targets.

1. C-Terminal Amide Peptide Synthesis

Rink Amide Linker supports C-terminal amide peptide construction in solid-phase peptide synthesis workflows used for research-grade peptide libraries and method development. The linker is engineered so the peptide chain is anchored through a resin attachment and released as a carboxamide, aligning with amino acid backbone chemistry where the C-terminal functionality is critical for amide bond formation and protease recognition studies. Cleavage converts the protected peptide-resin intermediate into the free peptide amide while preserving side-chain protecting groups appropriate to the chosen cleavage conditions. The resulting amide peptides can be used for peptide coupling chemistry optimization, reference material preparation, and structure-activity relationship studies that depend on terminal amide identity.

2. Protected Amino Acid Building Blocks

Rink Amide Linker is compatible with Fmoc-protected amino acid derivatives, making it suitable for workflows that emphasize controlled deprotection and peptide bond formation. The solid-phase format leverages the orthogonality between Fmoc removal and side-chain protection, while the linker's cleavage chemistry provides a defined route to convert the resin-bound carboxyl equivalent into a C-terminal amide. Side-chain functional groups such as serine, threonine, tyrosine, lysine, aspartate, glutamate, and cysteine derivatives can be incorporated using standard protecting-group strategies that remain stable through repeated coupling cycles. Downstream, the released peptides serve as biochemical research intermediates and analytical standards where terminal amide formation is required for consistent reactivity and characterization.

3. Peptidomimetic And SAR Libraries

Rink Amide Linker enables peptide and peptidomimetic scaffold generation where terminal amide presentation influences molecular recognition and conformational preferences. The linker's amide-forming release supports the synthesis of analog series that vary internal residues, side-chain modifications, or backbone constraints while keeping the C-terminal functional group constant. The resin-based approach supports parallel synthesis strategies for structure-activity relationship studies, including fragment-based optimization where amide-linked termini are used to probe binding motifs. Released peptide analogs and constrained derivatives can then be advanced into synthetic organic chemistry campaigns that require consistent C-terminal functionality for comparative evaluation.

4. Pharmaceutical Intermediate Preparation

Rink Amide Linker can be applied to the production of peptide intermediates used in fine chemical synthesis and pharmaceutical process development contexts where defined terminal functionality is required. The linker's role in converting a peptide chain into a C-terminal amide supports manufacturing-relevant reproducibility for intermediates that later undergo derivatization, conjugation, or further chemical transformations. Solid-phase handling can facilitate scalable purification strategies for peptide intermediates by enabling resin-based separation from soluble impurities during synthesis. Downstream products include peptide amide building blocks for process chemistry intermediate preparation, chemical manufacturing of peptide-derived reagents, and specialty chemical production of defined amide-containing structures.

5. Bioconjugation And Protein Engineering

Rink Amide Linker is suitable for generating peptide amide constructs used in bioconjugation chemistry and protein engineering workflows that require stable C-terminal amide termini. The linker facilitates synthesis of peptide segments that can present functional side chains for subsequent conjugation reactions, including protected or activated groups that can be unmasked post-synthesis depending on the protecting-group scheme. Amide-stabilized peptide segments can be used as recognition elements, linkers, or modular domains in protein engineering strategies where terminal amide identity affects assembly and stability. Released peptides can serve as biochemical research intermediates for conjugate formation, molecular labeling, and engineered biomolecule construction where controlled peptide chemistry underpins downstream reactivity.

Size
5 g;25 g;
InChI
1S/C32H29NO7/c1-37-22-15-16-27(29(17-22)38-2)31(20-11-13-21(14-12-20)39-19-30(34)35)33-32(36)40-18-28-25-9-5-3-7-23(25)24-8-4-6-10-26(24)28/h3-17,28,31H,18-19H2,1-2H3,(H,33,36)(H,34,35)
InChI Key
UPMGJEMWPQOACJ-UHFFFAOYSA-N
Canonical SMILES
COC1=CC(=C(C=C1)C(C2=CC=C(C=C2)OCC(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)OC

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