151132-82-0

Basic information

• Product Name: (2S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-[[(phenylmethoxy)carbonyl]amino]butanoic acid
• Synonyms: (2S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-[[(phenylmethoxy)carbonyl]amino]butanoic acid;N-Cbz-N'-Fmoc-L-2,4-Diaminobutyric acid;(S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-(((benzyloxy)methyl)amino)butanoic acid
• CAS NO: 151132-82-0
• Molecular Formula: C₂₇H₂₆N₂O₆
• Molecular Weight: 475
• Product Categories: amino acids
• Mol File: 151132-82-0.mol

Chemical Properties

• Boiling Point: 739.8±60.0 °C(Predicted)
• Appearance: /
• Density: 1.299
• Storage Temp.: 2-8°C
• PKA: 3.86±0.10(Predicted)
• CAS DataBase Reference: (2S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-[[(phenylmethoxy)carbonyl]amino]butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-[[(phenylmethoxy)carbonyl]amino]butanoic acid(151132-82-0)
• EPA Substance Registry System: (2S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-[[(phenylmethoxy)carbonyl]amino]butanoic acid(151132-82-0)

Safety Data

• Hazardous Substances Data: 151132-82-0(Hazardous Substances Data)

Usage

Uses

Used in Peptide Synthesis:
(2S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-[[(phenylmethoxy)carbonyl]amino]butanoic acid is used as a building block for the synthesis of peptides. The Fmoc protective groups allow for the controlled coupling of amino acids, ensuring that the desired peptide sequence is accurately formed. This is particularly important in the development of pharmaceuticals, where precise peptide sequences are required for specific biological activities.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (2S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-[[(phenylmethoxy)carbonyl]amino]butanoic acid is used as a key intermediate in the synthesis of therapeutic peptides. (2S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-[[(phenylmethoxy)carbonyl]amino]butanoic acid's structure and protective groups enable the creation of peptides with specific biological functions, such as targeting disease-causing proteins or modulating cellular processes.
Used in Research and Development:
(2S)-4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-[[(phenylmethoxy)carbonyl]amino]butanoic acid is also utilized in research settings to study the properties and potential applications of Fmoc-protected amino acids. This can lead to the discovery of new peptide-based drugs and therapeutic strategies, as well as a better understanding of the underlying chemistry involved in peptide synthesis.

InChI:InChI=1S/C27H26N2O6/c30-25(31)24(29-27(33)34-16-18-8-2-1-3-9-18)14-15-28-26(32)35-17-23-21-12-6-4-10-19(21)20-11-5-7-13-22(20)23/h1-13,23-24H,14-17H2,(H,28,32)(H,29,33)(H,30,31)/t24-/m0/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 62234-40-6 (2S)-2-{[(benzyloxy)carbonyl]amino}-4-(dimethylamino)butanoic acid 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 49855-91-6 2--4--L-2,4-diaminobutyric acid 
• 13907-82-9 N²-benzyloxycarbonyl-L-glutamine methyl ester 
• 182618-33-3 (S)-4-Amino-2-benzyloxycarbonylamino-butyric acid methyl ester 
• 3350-14-9 (S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-butyric acid methyl ester 
• 2650-64-8 Cbz-L-Gln 

Downstream Products

• 209269-95-4 (S)-3-[(S)-2-Benzyloxycarbonylamino-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyrylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid tert-butyl ester 
• 403736-51-6 [2-benzyloxycarbonylamino-4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyrylamino]-acetic acid tert-butyl ester 
• 403736-55-0 N_α-carbobenzyloxy-2,4-diamino-L-butyrylglycin tert-butyl ester 
• 403736-59-4 [2-benzyloxycarbonylamino-4-(3-methoxy-[1,2,4]thiadiazol-5-ylamino)-butyrylamino]-acetic acid tert-butyl ester 
• 151132-85-3 [(S)-3-Amino-1-(tetrahydro-pyran-2-yloxymethyl)-propyl]-carbamic acid benzyl ester 
• 151132-87-5 [((S)-3-Benzyloxycarbonylamino-4-hydroxy-butyl)-tert-butoxycarbonylmethyl-amino]-acetic acid tert-butyl ester 
• 151132-83-1 [(S)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-1-hydroxymethyl-propyl]-carbamic acid benzyl ester 
• 151132-88-6 (S)-2-Benzyloxycarbonylamino-4-(bis-tert-butoxycarbonylmethyl-amino)-butyric acid 
• 151132-86-4 {[(S)-3-Benzyloxycarbonylamino-4-(tetrahydro-pyran-2-yloxy)-butyl]-tert-butoxycarbonylmethyl-amino}-acetic acid tert-butyl ester 
• 151132-84-2 [(S)-3-(9H-Fluoren-9-ylmethoxycarbonylamino)-1-(tetrahydro-pyran-2-yloxymethyl)-propyl]-carbamic acid benzyl ester 

Relevant articles and documents

Synthesis and evaluation of novel dipeptide-bound 1,2,4-thiadiazoles as irreversible inhibitors of guinea pig liver transglutaminase.

Herein we report the synthesis and evaluation of 14 novel peptides as potential irreversible inactivators of guinea pig liver transglutaminase (TGase). These peptides were designed to resemble Cbz-L-Gln-Gly, known to be a good TGase substrate, and to include a 1,2,4-thiadiazole group. The side chain length of the amino acid residue bearing the inhibitor group was also varied in order to permit investigation of this effect. Their inactivation rate constants were measured using a direct continuous spectrophotometric method and were found to vary between 0.330 to 0.89 microM(-1) min(-1).

Modification of receptor selectivity and functional activity of cyclic cholecystokinin analogues

We reported earlier on the synthesis and biological activity at the CCK-B receptor of cyclized derivatives of CCK. These peptides, in which the positions 28 and 31 were replaced by lysine residues, were bridged by a succinyl moiety. To determine the importance of the nature and size of the cyclic structure, cyclic analogues were synthesized in which: (i) the lysine residues were replaced by ornithine and diaminobutyric acid and (ii) the succinic moiety was replaced by a malonic, adipic and glutaric moiety. They were tested For their ability to inhibit the specific binding of 125I-BH-CCK-8 to CCK receptors in rat pancreatic acini and guinea pig brain membranes. They were also evaluated for their ability to stimulate amylase secretion from rat pancreatic acini. The potency and selectivity of these analogues were compared with those obtained with CCK-4 and compound JIMV320, a potent and selective CCK-B receptor ligand synthesized earlier in our laboratory.

Metal Chelating Amino Acids in the Design of Peptides and Proteins. Synthesis of Nα-Fmoc/But Protected Amino Acids Incorporating Aminodiacetic Acid Moiety.

The synthesis of Fmoc/But protected amino acid chelators 14, 15, 16 and 24 is described.With respect to their Boc/Bzl derivatives, the title compounds offer synthetic advantage: peptide Ac-Ada(1)-Ala3-Ada(1)-Ala4-Glu-Lys-NH2 was assembled by So