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H-D-Glu-OMe is a protected form of D-Glutamic acid. D-Glutamic acid is an unnatural isomer of L-Glutamic acid, and is found in bacterial cell wall peptidoglycan of gram-positive and gram-negative bacteria. D-Glutamic acid also occurs as poly-gamma-Glutamic acid, which is a weak immunogen but is capable of acting as a hapten (a small molecule that induces the production of antibodies, as well as binding to them).

γ−Amino acids
Catalog number
CAS number
Molecular Formula
Molecular Weight
D-Glu-OMe; (R)-4-Amino-5-methoxy-5-oxopentanoic acid; (2s,4r)-methylglutamate; (4R)-4-amino-5-methoxy-5-oxopentanoic acid; D-Glu Ome
White to off-white powder
≥ 99% (HPLC)
1.242±0.06 g/cm3 (Predicted)
Melting Point
134-140 °C
Boiling Point
303.3±32.0 °C (Predicted)
Store at 2-8 °C
1. Derivatives of melphalan designed to enhance drug accumulation in cancer cells
L Kupczyk-Subotkowska, K Tamura, D Pal, T Sakaeda, T J Siahaan, V J Stella, R T Borchardt J Drug Target. 1997;4(6):359-70. doi: 10.3109/10611869709017893.
The objective of this study was to develop chemical strategies to improve the uptake and accumulation of melphalan (L-Mel and D-Mel), a cytotoxic agent, into cancer cells. Dipeptides synthesized from L- (or D-) Mel and L-glutamic acid (L-Glu) or L-valine (L-Val) and their methyl or ethyl esters (all compounds were trifluoroacetic acid salts) were evaluated for cytotoxicity and cellular uptake using Caco-2 cells, a human colon carcinoma cell line, and RT-2 cells, a rat brain glioma cell line. Treatment of Caco-2 cells with L-Mel or D-Mel (0.5 mg/ml equivalent of melphalan) for 48 h resulted in approximately 50% cell survival. Treatment of the Caco-2 cells with dipeptide derivatives of L-Mel (or D-Mel) (11c-d, 12c-d and 13) caused similar cytotoxicity effects (approximately 50-70% of cell survival). When the cytotoxicities of the esters of L-Mel, D-Mel and their dipeptide derivatives (11a-b, 12a-b and 14) in Caco-2 cells were determined, less than 10% cell survival was observed. Similar results were observed in RT-2 cells. When the cellular uptake properties of these compounds were determined in Caco-2 cell monolayers, L-Glu-L-Mel (12c), L-Glu-D-Mel (12d), and L-Mel-L-Glu (11c) generated slightly lower intracellular levels of L-Mel or D-Mel than when the cell monolayer was treated with the amino acids (L-Mel or D-Mel). In Caco-2 cells treated with 11c, 12c or 12d, low levels of the dipeptides were also detected. Caco-2 cell monolayers treated with D-Mel-L-Glu (11d) or D-Mel-L-Val (13) showed very low levels of the amino acids (L-Mel or D-Mel), but generally higher levels of the dipeptides. In contrast to the amino acids (L-Mel, D-Mel) or the dipeptide derivatives (11c-d, 12c-d and 13), the ester derivatives of the amino acids [L-Mel(OEt), D-Mel(OEt)] or the dipeptides (11a-b, 12a-b and 14) produced 5-20 times higher intracellular concentrations of potentially cytotoxic metabolites (e.g., L-Mel, D-Mel, Mel-containing dipeptides or Mel-containing dipeptide monoesters). L-Mel(OEt), D-Mel(OEt), L-Glu(OEt)-L-Mel(OEt) (12a), L-Glu(OEt)-D-Mel(OEt) (12b), and L-Mel-L-Glu(OEt)2 (11a) accumulated mainly as either L-Mel or D-Mel, and the percentages of L-Mel or D-Mel were 99%, 99%, 90%, 75% and 98% of the total intracellular concentration of potentially cytotoxic agents, respectively. D-Mel-L-Glu(OEt)2 (11b) accumulated as its monoester (> 95%) and D-Mel-L-Val(OMe) (14) accumulated as its dipeptide metabolite (> 98%). Inclusion of Gly-Pro, carnosine, L-Phe or L-Glu did not inhibit uptake of the dipeptide derivatives of L-Mel (or D-Mel) or their esters. These results suggest that the cellular uptake of the dipeptide derivatives of melphalan and their esters is probably via passive diffusion rather than being facilitated by an amino acid transporter or a di/tripeptide transporter. The higher intracellular levels of cytotoxic agents generated from the ester derivatives of the amino acids and the dipeptides are probably due to their higher lipophilicity and the overall neutral charge of the esters and subsequent intracellular formation of the more polar amino acids (L- or D-Mel) and/or Mel-containing dipeptides. Finally, these studies suggest that dipeptides of D-Mel [11b, 11d, 13] have inherent cytotoxicity properties.
2. Artificial Pancreas Systems for People With Type 2 Diabetes: Conception and Design of the European CLOSE Project
Freimut Schliess, et al. J Diabetes Sci Technol. 2019 Mar;13(2):261-267. doi: 10.1177/1932296818803588. Epub 2018 Sep 21.
In the last 10 years tremendous progress has been made in the development of artificial pancreas (AP) systems for people with type 1 diabetes (T1D). The pan-European consortium CLOSE (Automated Glu cose Contro l at H ome for People with Chronic Disea se) is aiming to develop integrated AP solutions (APplus) tailored to the needs of people with type 2 diabetes (T2D). APplus comprises a product and service package complementing the AP system by obligatory training as well as home visits and telemedical consultations on demand. Outcome predictors and performance indicators shall help to identify people who could benefit most from AP usage and facilitate the measurement of AP impact in diabetes care. In a first step CLOSE will establish a scalable APplus model case working at the interface between patients, homecare service providers, and payers in France. CLOSE will then scale up APplus by pursuing geographic distribution, targeting additional audiences, and enhancing AP functionalities and interconnectedness. By being part of the European Institute of Innovation and Technology (EIT) Health public-private partnership, CLOSE is committed to the EIT "knowledge triangle" pursuing the integrated advancement of technology, education, and business creation. Putting stakeholders, education, and impact into the center of APplus advancement is considered key for achieving wide AP use in T2D care.
3. Analysis of "Artificial Pancreas (AP) Systems for People With Type 2 Diabetes: Conception and Design of the European CLOSE Project"
Andrew A Bremer, Guillermo Arreaza-Rubín J Diabetes Sci Technol. 2019 Mar;13(2):268-270. doi: 10.1177/1932296818823770. Epub 2019 Jan 19.
In an article in Journal of Diabetes Science and Technology, Schliess and coauthors describe the conception and design of the European Automated Glu cose Contro l at H ome for People with Chronic Di sease (CLOSE) initiative for the implementation of artificial pancreas (AP) systems for people with diabetes. The CLOSE consortium aims to develop integrated AP solutions (APplus) tailored to the needs of individuals with type 2 diabetes (T2D) by developing superior risk- and cost-benefit scenarios for AP operation to achieve acceptance by users and caregivers and a high likelihood for reimbursement. CLOSE is integrating the AP platform into the center of a comprehensive product and service package specifically tailored to defined T2D patient groups and care environments, leading to an interactive collaboration with users, health care providers, and other stakeholders in diabetes care. This is a very ambitious but well-conceived and delineated project which takes into consideration most of the relevant factors that may influence AP implementation in T2D care.

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