Boc-L-4-trans-hydroxyproline methyl ester
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Boc-L-4-trans-hydroxyproline methyl ester

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Boc-L-4-trans-hydroxyproline methyl ester is a non-cleavable ADC linker and also an alkyl chain-based PROTAC linker.

Category
BOC-Amino Acids
Catalog number
BAT-007100
CAS number
74844-91-0
Molecular Formula
C11H19NO5
Molecular Weight
245.27
Boc-L-4-trans-hydroxyproline methyl ester
IUPAC Name
1-O-tert-butyl 2-O-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
Synonyms
Boc-L-Hyp-OMe; 1-tert-Butyl-2-methyl; (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate; Boc L Hyp OMe
Appearance
White Powder
Purity
>95% by GC
Density
1.2±0.1 g/cm3
Melting Point
96 °C
Boiling Point
335.2±42.0 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m1/s1
InChI Key
MZMNEDXVUJLQAF-SFYZADRCSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1CC(CC1C(=O)OC)O
1. Alginate ester: New moisture-scavenging excipients for direct compressible pharmaceutical tableting
Noelia M Sanchez-Ballester, Philippe Trens, Jean-Christophe Rossi, Ian Soulairol Carbohydr Polym. 2022 Dec 1;297:120063. doi: 10.1016/j.carbpol.2022.120063. Epub 2022 Aug 31.
The objective of this work is to evaluate methyl ester alginates and alginic acid (AA) as moisture-scavenging excipients for the formulation of aspirin tablets obtained by direct compression. The tablets were stored at accelerated conditions (40 °C/75 % RH) and assessed for changes in tensile strength, mass, thickness and disintegration time. While moisture caused a reduction in the hardness of MCC and AA tablets, hardness of the tablets made from methylated materials was virtually unaffected. The physical stability of alginate ester tablets was found to be related to their increased plastic deformation leading to extended interparticle contact with less impact on tablet porosity. Finally, the combination of higher moisture affinity and lower water dissociation exhibited by alginates esters resulted in tablets with the lowest aspirin degradation. These findings suggest that excipients with high water retention can act as moisture-scavengers without losing their functional properties and reducing the degradation of moisture-sensitive drugs.
2. O-Methylation of carboxylic acids with streptozotocin
Li-Yan Zeng, Yang Liu, Jiakun Han, Jinhong Chen, Shuwen Liu, Baomin Xi Org Biomol Chem. 2022 Jul 6;20(26):5230-5233. doi: 10.1039/d2ob00578f.
The clinically used DNA-alkylating drug streptozotocin (STZ) was investigated using a simple work-up as an O-methylating agent to transform various carboxylic acids, sulfonic acids and phosphorous acids into corresponding methyl esters, and did so with yields of up to 97% in 4 h at room temperature. Good substrate tolerance was observed, and benefited from the mild conditions and compatibility of the reaction with water.
3. Acridinium Ester Chemiluminescence: Methyl Substitution on the Acridine Moiety
Manabu Nakazono, Shinkoh Nanbu, Takeyuki Akita, Kenji Hamase J Oleo Sci. 2021;70(11):1677-1684. doi: 10.5650/jos.ess21186.
Methyl groups were introduced on the acridine moiety in chemiluminescent acridinium esters that have electron-withdrawing groups (trifluoromethyl, cyano, nitro, ethoxycarbonyl) at the 4-position on the phenyl ester. The introduction of methyl groups at the 2-, 2,7-, and 2,3,6,7-positions on the acridine moiety shifted the optimal pH that gave relatively strong chemiluminescence intensity from neutral conditions to alkaline conditions. 4-(Ethoxycarbonyl)phenyl 2,3,6,7,10-pentamethyl-10λ4-acridine-9-carboxylate, trifluoromethanesulfonate salt showed long-lasting chemiluminescence under alkaline conditions. Acridinium esters to determine hydrogen peroxide concentration at pH 7-10 were newly developed.
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