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FMOC-D-alanine, also known as N-(9-fluorenylmethoxycarbonyl)-D-alanine, is a non-natural, chiral amino acid derivative that plays a significant role in various scientific and industrial applications. It is characterized by the presence of a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group, which is crucial for its functionality in peptide synthesis and other related processes.

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  • 79990-15-1 Structure
  • Basic information

    1. Product Name: FMOC-D-alanine
    2. Synonyms: (R)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PROPIONIC ACID;N-FMOC-D-ALANINE HYDRATE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-D-ALANINE, MONOHYDRATE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-ALANINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-ALANINE MONOHYDRATE;N-[(9H-FLUOREN-9YLMETHOXY)CARBONYL]-D-ALANINE;N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-D-ALANINE HYDRATE;N-9-FLUORENYLMETHOXYCARBONYL-D-ALANINE
    3. CAS NO:79990-15-1
    4. Molecular Formula: C18H17NO4
    5. Molecular Weight: 311.33
    6. EINECS: 1533716-785-6
    7. Product Categories: Fluorenes, Flurenones;Amino Acids;Alanine [Ala, A];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series
    8. Mol File: 79990-15-1.mol
  • Chemical Properties

    1. Melting Point: 151-155 °C
    2. Boiling Point: 544.1 °C at 760 mmHg
    3. Flash Point: 282.9 °C
    4. Appearance: white to off-white crystalline powder
    5. Density: 1.282 g/cm3
    6. Vapor Pressure: 1.13E-12mmHg at 25°C
    7. Refractive Index: 19 ° (C=1, DMF)
    8. Storage Temp.: 2-8°C
    9. Solubility: DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
    10. PKA: 3.91±0.10(Predicted)
    11. Water Solubility: Soluble in dimethylformamide (1 mole in 2 ml). Insoluble in water.
    12. BRN: 8025133
    13. CAS DataBase Reference: FMOC-D-alanine(CAS DataBase Reference)
    14. NIST Chemistry Reference: FMOC-D-alanine(79990-15-1)
    15. EPA Substance Registry System: FMOC-D-alanine(79990-15-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 79990-15-1(Hazardous Substances Data)

79990-15-1 Usage

Uses

Used in Proteomics Studies:
FMOC-D-alanine is used as a research tool in proteomics studies for the analysis and identification of proteins. Its unique properties allow for the selective detection and quantification of specific protein sequences, contributing to a better understanding of protein functions and interactions within biological systems.
Used in Solid Phase Peptide Synthesis Techniques:
In the field of peptide chemistry, FMOC-D-alanine is utilized as a key building block in solid phase peptide synthesis (SPPS) techniques. The Fmoc group serves as a temporary protecting group for the amino acid's side chain, enabling the stepwise assembly of peptide chains on an insoluble resin support. This method allows for the efficient and controlled synthesis of peptides and has been widely adopted in both research and commercial applications.
Used in Pharmaceutical Industry:
FMOC-D-alanine is used as a starting material for the synthesis of various pharmaceutical compounds, including antibiotics, immunosuppressants, and other therapeutic agents. Its unique stereochemistry and reactivity make it a valuable component in the development of novel drugs with improved efficacy and selectivity.
Used in Bacterial Cell Wall Synthesis:
FMOC-D-alanine is essential for the biosynthesis of peptidoglycan cross-linking sub-units that are used for bacterial cell walls. This makes it a critical component in the development of new antibiotics targeting bacterial cell wall synthesis, potentially leading to the discovery of more effective treatments for bacterial infections.

Check Digit Verification of cas no

The CAS Registry Mumber 79990-15-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,9,9,9 and 0 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 79990-15:
(7*7)+(6*9)+(5*9)+(4*9)+(3*0)+(2*1)+(1*5)=191
191 % 10 = 1
So 79990-15-1 is a valid CAS Registry Number.
InChI:InChI=1/C18H17NO4/c1-11(17(20)21)19-18(22)23-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16H,10H2,1H3,(H,19,22)(H,20,21)/t11-/m1/s1

79990-15-1 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (F0596)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-alanine Hydrate  >98.0%(HPLC)(T)

  • 79990-15-1

  • 5g

  • 490.00CNY

  • Detail
  • TCI America

  • (F0596)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-alanine Hydrate  >98.0%(HPLC)(T)

  • 79990-15-1

  • 25g

  • 1,650.00CNY

  • Detail
  • Alfa Aesar

  • (H62395)  N-Fmoc-D-alanine, 95%   

  • 79990-15-1

  • 5g

  • 616.0CNY

  • Detail
  • Alfa Aesar

  • (H62395)  N-Fmoc-D-alanine, 95%   

  • 79990-15-1

  • 25g

  • 2772.0CNY

  • Detail
  • Aldrich

  • (47508)  Fmoc-D-Ala-OH  ≥98.0% (HPLC)

  • 79990-15-1

  • 47508-5G

  • 1,043.64CNY

  • Detail

79990-15-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid

1.2 Other means of identification

Product number -
Other names FMOC-N-D-alanine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:79990-15-1 SDS

79990-15-1Relevant articles and documents

Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety

Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong

, p. 1080 - 1090 (2020/05/25)

Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.

Determination of Chemical and Enantiomeric Purity of α-Amino Acids and their Methyl Esters as N-Fluorenylmethoxycarbonyl Derivatives Using Amylose-derived Chiral Stationary Phases

Islam, Md. Fokhrul,Adhikari, Suraj,Paik, Man-Jeong,Lee, Wonjae

, p. 332 - 338 (2019/04/13)

Liquid chromatographic enantiomer separation and simultaneous determination of chemical and enantiomeric purity of α-amino acids and their methyl esters as N-fluorenylmethoxycarbonyl (FMOC) derivatives was performed on three covalently bonded type chiral stationary phases (CSPs) derived from amylose derivatives. The enantiomer separation of α-amino acid esters as N-FMOC derivatives was better than that of the corresponding acids, especially for CSP 1 and 2. Chemical impurities as the corresponding racemic acids present in several commercially available racemic amino acid methyl esters were observed to be 0.49–17.50%. Enantiomeric impurities of several commercially available L-amino acid methyl esters were found to be 0.03–0.58%, whereas chemical impurities as the corresponding racemic acids present in the same analytes were found to be 0.13–13.62%. This developed analytical method will be useful for the determination of chemical and enantiomeric purity of α-amino acids and/or esters as N-FMOC derivatives using amylose-derived CSPs.

Structure-guided engineering of: Meso -diaminopimelate dehydrogenase for enantioselective reductive amination of sterically bulky 2-keto acids

Cheng, Xinkuan,Chen, Xi,Feng, Jinhui,Wu, Qiaqing,Zhu, Dunming

, p. 4994 - 5002 (2018/10/17)

meso-Diaminopimelate dehydrogenase (DAPDH) and mutant enzymes are an excellent choice of biocatalysts for the conversion of 2-keto acids to the corresponding d-amino acids. However, their application in the enantioselective reductive amination of bulky 2-keto acids, such as phenylglyoxylic acid, 2-oxo-4-phenylbutyric acid, and indole-3-pyruvic acid, is still challenging. In this study, the structure-guided site-saturation mutagenesis of a Symbiobacterium thermophilum DAPDH (StDAPDH) gave rise to a double-site mutant W121L/H227I, which showed dramatically improved enzyme activities towards various 2-keto acids including these sterically bulky substrates. Several d-amino acids were prepared in optically pure form. The molecular docking of substrates into the active sites of wild-type and mutant W121L/H227I enzymes revealed that the substrate binding cavity of the mutant enzyme was reshaped to accommodate these bulky substrates, thus leading to higher enzyme activity. These results lay a foundation for further shaping the substrate binding pocket and manipulating the interactions between the substrate and binding sites to access highly active d-amino acid dehydrogenases for the preparation of synthetically challenging d-amino acids.

Synthesis and biological evaluation of novel FK228 analogues as potential isoform selective HDAC inhibitors

Narita, Koichi,Matsuhara, Keisuke,Itoh, Jun,Akiyama, Yui,Dan, Singo,Yamori, Takao,Ito, Akihiro,Yoshida, Minoru,Katoh, Tadashi

, p. 592 - 609 (2016/07/06)

Novel C4- and C7-modified FK228 analogues were efficiently synthesized in a highly convergent and unified manner. This synthesis features the amide condensation of glycine-d-cysteine-containing segments with d-valine-containing segments for the direct assembly of the corresponding seco-acids, which are key precursors of macrolactones. The HDAC inhibition assay and cell-growth inhibition analysis of the synthesized analogues revealed novel aspects of their structure-activity relationship. This study demonstrated that simple modification at the C4 and C7 side chains in FK228 is effective for improving both HDAC inhibitory activity and isoform selectivity; moreover, potent and highly isoform-selective class I HDAC1 inhibitors were identified.

Reversible hydrogen transfer between cysteine thiyl radical and glycine and alanine in model peptides: Covalent H/D exchange, radical-radical reactions, and l - To D -Ala conversion

Mozziconacci, Olivier,Kerwin, Bruce A.,Sch?neich, Christian

experimental part, p. 6751 - 6762 (2011/01/03)

The reversible intramolecular hydrogen transfer reaction of peptide Cys thiyl radicals with Gly and Ala residues was studied in model peptides, where thiyl radicals were either generated through photochemical cleavage of disulfide bonds or through the rea

Total synthesis of (+)-azinothricin and (+)-kettapeptin

Hale, Karl J.,Manaviazar, Soraya,George, Jonathan H.,Walters, Marcus A.,Dalby, Stephen M.

supporting information; experimental part, p. 733 - 736 (2009/09/30)

(Chemical Equation Presented) Asymmetric total syntheses of (+)-azinothricin and (+)-kettapeptin have been completed through a common new pathway that exploits a highly chemoselective coupling reaction between the fully elaborated cyclodepsipeptide 5 and the glycal activated esters 3 and 4 at the final stages of both respective syntheses.

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