111662-65-8

Basic information

• Product Name: FMOC-D-GLA(OTBU)2-OH
• Synonyms: FMOC-D-GLA(OTBU)2-OH;FMOC-D-4-CARBOXYGLUTAMIC ACID DI-TERT BUTYLESTER;FMOC-D-4-CARBOXYLGLUTAMIC ACID DI-TERT-BUTYL ESTER;FMOC-GAMMA-CARBOXY-D-GLU(OTBU)2-OH;FMOC-GAMMA-CARBOXY-D-GLUTAMIC ACID GAMMA,GAMMA-DI-T-BUTYL ESTER;FMOC-GAMMA-CARBOXY-D-GLUTAMIC ACID(OTBU)2-OH;FMOC-GAMMA-CARBOXY-GAMMA-(DI-T-BUTYL ESTER)-D-GLUTAMIC ACID;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-GAMMA-CARBOXY-D-GLUTAMIC-ACID-GAMMA-DI-T-BUTYL ESTER
• CAS NO: 111662-65-8
• Molecular Formula: C29H35NO8
• Molecular Weight: 525.59
• Product Categories: amino acids
• Mol File: 111662-65-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 695.328 °C at 760 mmHg
• Flash Point: 374.321 °C
• Appearance: /
• Density: 1.217 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: -15°C
• PKA: 3.50±0.10(Predicted)
• CAS DataBase Reference: FMOC-D-GLA(OTBU)2-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-GLA(OTBU)2-OH(111662-65-8)
• EPA Substance Registry System: FMOC-D-GLA(OTBU)2-OH(111662-65-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 111662-65-8(Hazardous Substances Data)

Usage

Uses

Fmoc-D-Gla(OtBu)2-OH is a protected form of carboxyglutamic acid used in the synthetic preparation of peptides and peptide fragments, such as cyclic RGD pentapeptides.

InChI:InChI=1/C29H35NO8/c1-28(2,3)37-25(33)21(26(34)38-29(4,5)6)15-23(24(31)32)30-27(35)36-16-22-19-13-9-7-11-17(19)18-12-8-10-14-20(18)22/h7-14,21-23H,15-16H2,1-6H3,(H,30,35)(H,31,32)/t23-/m1/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 86633-09-2 di-tert-butyl methylenemalonate 
• 56-40-6 glycine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 56877-44-2 γ,γ'-Di-tert-butyl-DL-γ-carboxyglutamic acid 
• 56877-43-1 N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-D-γ-carboxyglutamic acid 
• 56877-40-8 Z-γ,γ,-di-tert-butyl-D,L-carboxyglutamic acid methyl ester 
• 541-16-2 t-butyl malonate 
• 60686-53-5 γ,γ'-di-tert-butyl-D-γ-carboxyglutamic acid 
• 181637-44-5 (S)-1-benzyl-5,5'-di-tert-butyl-N-(triphenylmethyl)-4-carboxyglutamate 
• 873310-66-8 4-benzyloxycarbonylamino-2-tert-butoxycarbonyl-pent-2-enedioic acid 1-tert-butyl ester 
• 873310-65-7 2S-(2-benzyloxycarbonylamino-3-hydroxy-propylidene)-malonic acid di-tert-butyl ester 
• 60686-50-2 N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-L-γ-carboxyglutamic acid 
• 912354-29-1 (4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-tert-butyl ester 

Relevant articles and documents

Improved chemical synthesis of optically pure N-(9-fluorenylmethoxycarbonyl)-γ,γ′-di-tert-butyl-γ- carboxyglutamic acid

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A practical synthesis of fully protected L-γ-carboxyglutamic acid

We have developed a new synthetic route for the preparation of Fmoc protected L-γ-carboxyglutamic acid in 60% overall yield (>99% ee) via a six-step synthesis from D-Garner's aldehyde. An aldol condensation and the selective cleavage of the acetonide prot

The synthesis and properties of Gla- and Phe-containing analogues of cyclic RGD pentapeptides

Cyclopentapeptides containing the Arg-Gly-Asp motif have been synthesised using solid-phase assembly of side-chain-protected linear precursors, followed by solution-phase cyclisation. The replacement of the Asp residue by γ-carboxyglutamic acid (Gla) is a novel feature which gives rise to an analogue which inhibits cell adhesion, yet its congeners do not show activity in binding assays with recombinant integrin receptors. NMR techniques support a β/γ-turn conformation in most of the analogues. The Royal Society of Chemistry 2000.