Fmoc-Ile-OH: Properties, Uses & Handling FAQ

2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-methylpentanoicacid is a Fmoc-protected derivative of L-isoleucine widely employed as a building block in solid-phase peptide synthesis (SPPS).

IUPAC Name

2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-methylpentanoic acid

Common Abbreviation

Fmoc-Ile-OH

Protecting Group

Fmoc (9-fluorenylmethoxycarbonyl) on the alpha-amine

Primary Application

Solid-phase peptide synthesis (SPPS) as an isoleucine residue building block

Fmoc Deprotection Condition

Piperidine in DMF (typically 20% v/v)

Catalog SKU

M695362

What Is Fmoc-Ile-OH and Why Is It Used in Peptide Synthesis?

2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-methylpentanoic acid, commonly known as Fmoc-Ile-OH, is the Fmoc-protected form of the essential branched-chain amino acid L-isoleucine. The 9-fluorenylmethoxycarbonyl (Fmoc) group shields the alpha-amine during peptide bond formation, preventing unwanted side reactions and enabling sequential, controlled chain elongation.

In solid-phase peptide synthesis (SPPS), Fmoc-Ile-OH is coupled to a resin-bound growing peptide chain using standard activating reagents. After each coupling step, the Fmoc group is removed under mild basic conditions, exposing the free amine for the next coupling cycle. This iterative protect–couple–deprotect strategy allows researchers to assemble complex peptides with high fidelity.

Storage, Stability, and Solubility

Fmoc-Ile-OH should be stored in a cool, dry, and well-ventilated location away from light, heat, and moisture to preserve integrity. The compound is generally stable under recommended storage conditions; however, prolonged exposure to humidity or elevated temperatures may lead to gradual degradation of the Fmoc protecting group.

For solubility, Fmoc-Ile-OH is readily soluble in common polar aprotic solvents used in SPPS workflows, including dimethylformamide (DMF) and dimethyl sulfoxide (DMSO). It also shows solubility in dichloromethane (DCM). Researchers should prepare fresh solutions prior to use and avoid storing dissolved reagent for extended periods to maintain coupling efficiency.

Handling, Safety, and Regulatory Considerations

When handling Fmoc-Ile-OH, standard laboratory safety practices apply. Researchers should wear appropriate personal protective equipment (PPE), including gloves, lab coat, and eye protection. Avoid inhalation of dust or aerosols. Work in a well-ventilated area or fume hood when weighing or preparing solutions.

Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use for comprehensive hazard, first-aid, and disposal information specific to this reagent. Dispose of chemical waste in accordance with local institutional and regulatory guidelines.

Quality, Purity, and Ordering Information

Aladdin Scientific offers 2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-methylpentanoic acid under catalog number M695362. Researchers and procurement staff should verify the purity specification on the Certificate of Analysis (CoA) accompanying each lot, as high purity is critical for achieving reliable coupling yields and final peptide quality in SPPS workflows.

For bulk quantities, custom packaging, or additional technical information, contact Aladdin Scientific's customer service or your regional sales representative. Lot-specific documentation, including CoA and SDS, is available upon request.

Frequently asked questions

What is the role of the Fmoc group in 2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-methylpentanoic acid?

The Fmoc (9-fluorenylmethoxycarbonyl) group serves as a temporary protecting group for the alpha-amine of isoleucine. It prevents undesired reactions at the amine during peptide coupling steps and is selectively removed using a mild base such as 20% piperidine in DMF, making it ideal for Fmoc-based SPPS strategies.

Which solvents are suitable for dissolving Fmoc-Ile-OH (M695362) in the laboratory?

Fmoc-Ile-OH is generally soluble in polar aprotic solvents commonly used in SPPS, including DMF, DMSO, and DCM. Fresh solutions should be prepared before use to ensure optimal reagent activity and coupling performance.

How should Fmoc-Ile-OH be stored to maintain its stability?

The compound should be stored in a cool, dry, and well-ventilated area, protected from light and moisture. Proper storage conditions help prevent degradation of the Fmoc protecting group and maintain the reagent's suitability for peptide synthesis applications.

What coupling reagents are compatible with Fmoc-Ile-OH in SPPS?

Fmoc-Ile-OH is compatible with standard SPPS coupling reagents such as HATU, HBTU, DIC/HOBt, and PyBOP, among others. The choice of coupling reagent may depend on the specific resin, sequence, and scale of synthesis being undertaken.

Where can I find the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for M695362?

Lot-specific CoA and SDS documents for M695362 are available from Aladdin Scientific. You can request these documents through the product page on the Aladdin Scientific website or by contacting customer service directly.

References

1. Fields, G.B.; Noble, R.L. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. International Journal of Peptide and Protein Research, 1990.
2. Carpino, L.A.; Han, G.Y. The 9-fluorenylmethoxycarbonyl function, a new base-sensitive amino-protecting group. Journal of the American Chemical Society, 1972.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.