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Fmoc-(Fmoc-Hmb)-Ala-OH

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

Fmoc-Amino Acids

Catalog number

BAT-005288

CAS number

148515-85-9

Molecular Formula

C41H35NO8

Molecular Weight

669.72

IUPAC Name

(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl-[[2-(9H-fluoren-9-ylmethoxycarbonyloxy)-4-methoxyphenyl]methyl]amino]propanoic acid

Synonyms

N-ALPHA-FMOC-N-ALPHA-(2-FMOC-OXY-4-METHOXYBENZYL)-L-ALANINE; N-ALPHA-FMOC-N-ALPHA-(2-FMOC-OXY-4-METHOXYBENZYL)-ALANINE; FMOC-[2-N-ALPHA-FMOC-OXY-4-METHOXYBENZYL]-L-ALANINE; FMOC-(FMOCHMB)ALA-OH; FMOC-(FMOC-O-PMEOBZL)ALA-OH; (S)-2-((((9H-fluoren-9-yl)methyl9H-

Purity

≧ 95%

Density

1.311±0.060 g/cm3

Boiling Point

857.9±65.0 °C

InChI

InChI=1S/C41H35NO8/c1-25(39(43)44)42(40(45)48-23-36-32-15-7-3-11-28(32)29-12-4-8-16-33(29)36)22-26-19-20-27(47-2)21-38(26)50-41(46)49-24-37-34-17-9-5-13-30(34)31-14-6-10-18-35(31)37/h3-21,25,36-37H,22-24H2,1-2H3,(H,43,44)/t25-/m0/s1

InChI Key

NABBLRADDJWAHI-VWLOTQADSA-N

Canonical SMILES

CC(C(=O)O)N(CC1=C(C=C(C=C1)OC)OC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)OCC5C6=CC=CC=C6C7=CC=CC=C57

Fmoc-(Fmoc-Hmb)-Ala-OH is a specialized derivative used in peptide synthesis to protect amino acids during the assembly process. Here are some key applications of Fmoc-(Fmoc-Hmb)-Ala-OH:

Solid-Phase Peptide Synthesis (SPPS): This compound is widely used in SPPS to protect the amino-terminus of alanine residues during peptide assembly. Its use helps in preventing side reactions that may compromise the overall yield and purity of the synthesized peptide. The Fmoc group can be easily removed under mildly basic conditions, facilitating efficient elongation of the peptide chain.

Peptidomimetic Research: In the development of peptidomimetics, Fmoc-(Fmoc-Hmb)-Ala-OH is used to incorporate alanine residues with specific protection into synthetic peptide analogs. This assists in studying interactions between peptides and target proteins, which is crucial for drug design and development. By using this derivative, researchers can systematically modify and optimize peptide structures to enhance their stability and bioactivity.

Studying Peptide Folding and Stability: Fmoc-(Fmoc-Hmb)-Ala-OH is employed in creating peptides for studies focused on understanding peptide folding and stability. The dual Fmoc protecting groups help in stabilizing the peptide backbone during synthesis, allowing researchers to produce peptides that can be used to study secondary and tertiary structures. Insights gained from these studies are vital for applications in protein engineering and design.

Combinatorial Chemistry: In combinatorial chemistry, Fmoc-(Fmoc-Hmb)-Ala-OH is utilized to build diverse peptide libraries. The efficient and reversible protection it offers enables the rapid synthesis of numerous peptide variants on solid supports. This approach is key in high-throughput screening for discovering new bioactive peptides and therapeutic candidates.

1. Identification of Fmoc-beta-Ala-OH and Fmoc-beta-Ala-amino acid-OH as new impurities in Fmoc-protected amino acid derivatives

E Hlebowicz, A J Andersen, L Andersson, B A Moss J Pept Res. 2005 Jan;65(1):90-7. doi: 10.1111/j.1399-3011.2004.00201.x.

During the manufacture of a proprietary peptide drug substance a new impurity appeared unexpectedly. Investigation of its chemical structure established the impurity as a beta-Ala insertion mutant of the mother peptide. The source of the beta-Ala was identified as contamination of the Fmoc-Ala-OH raw material with Fmoc-beta-Ala-Ala-OH. Further studies also demonstrated the presence of beta-Ala in other Fmoc-amino acids, particularly in Fmoc-Arg(Pbf)-OH. In this case, it was due to the presence of both Fmoc-beta-Ala-OH and Fmoc-beta-Ala-Arg(Pbf)-OH. It is concluded that beta-Ala contamination of Fmoc-amino acid derivatives is a general and hitherto unrecognized problem to suppliers of Fmoc-amino acid derivatives. The beta-Ala is often present as Fmoc-beta-Ala-OH and/or as a dipeptide, Fmoc-beta-Ala-amino acid-OH. In collaboration with the suppliers, new specifications were introduced, recognizing the presence of beta-Ala-related impurities in the raw materials and limiting them to acceptable levels. The implementation of these measures has essentially eliminated beta-Ala contamination as a problem in the manufacture of the drug substance.

2. High-Quality Conjugated Polymers Achieving Ultra-Trace Detection of Cr2O72- in Agricultural Products

Hui Li, Fei Li, Fang Liu, Xiao Chen, Wenyuan Xu, Liang Shen, Jingkun Xu, Rui Yang, Ge Zhang Molecules. 2022 Jul 4;27(13):4294. doi: 10.3390/molecules27134294.

In view of that conjugated polymers (CPs) are an attractive option for constructing high-sensitive Cr2O72- sensors but suffer from lacking a general design strategy, we first proposed a rational structure design of CPs to tailor their sensing properties while validating the structure-to-performance correlation. Short side chains decorated with N and O atoms as recognition groups were instructed into fluorene to obtain monomers Fmoc-Ala-OH and Fmoc-Thr-OH. Additionally, their polymers P(Fmoc-Ala-OH) and P(Fmoc-Thr-OH) were obtained through electrochemical polymerization. P(Fmoc-Ala-OH) and P(Fmoc-Thr-OH) with high polymerization degrees have an excellent selectivity towards Cr2O72- in comparison to other cations and anions. Additionally, their limit of detection could achieve 1.98 fM and 3.72 fM, respectively. Especially, they could realize the trace detection of Cr2O72- in agricultural products (red bean, black bean, and millet). All these results indicate that short side chains decorated with N and O atoms functionalizing polyfluorene enables the ultra-trace detection of Cr2O72-. Additionally, the design strategy will spark new ideas for the construction of highly selective and sensitive Cr2O72- sensors.

3. Formation of Fmoc-beta-alanine during Fmoc-protections with Fmoc-OSu

Markus Obkircher, Christian Stähelin, Fritz Dick J Pept Sci. 2008 Jun;14(6):763-6. doi: 10.1002/psc.1001.

During the Fmoc-protection of H-alpha-Me-Val-OH, an unknown side product was found and isolated. The characterization using various analytical methods led unambiguously to the result that Fmoc-beta-Ala-OH was formed during the reaction. The reagent Fmoc-OSu was proven to be the source of Fmoc-beta-Ala-OH, following a mechanism that involved many deprotonation and elimination steps and a Lossen-type rearrangement as key sequence. The impurity Fmoc-beta-Ala-OH was found in a variety of reactions in which Fmoc-OSu was applied, either in the reaction mixture or as a contamination of the crude product. Purification of the Fmoc-amino acid derivatives from this impurity incurred high costs and significant reductions in yield.