368424-95-7

Upstream product

• 50-00-0 formaldehyd 
• 39994-75-7 L-threonine methyl ester hydrochloride 
• 3373-59-9 L-threonine methyl ester 
• 110-88-3 1,3,5-Trioxan 

Downstream Products

• 95599-23-8 N-methyl-L-threonine methyl ester 

Relevant academic research and scientific papers

THERAPEUTIC COMPOUNDS AND METHODS OF USE THEREOF

The invention provides compounds having the general Formula (I); and pharmaceutically acceptable salts thereof; wherein the variables RA, RAA, subscript n, subscript q, ring A, X2, L, subscript m, X1, R1, R2, R3, R4, R5, D and E have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

Conversion of isomeric 2:3 adducts (aminoacid-formaldehyde) to N-acyl-pseudoprolines derivatives

Reaction of acyl chlorides or acid anhydrides with isomeric 2:3 adducts derived from condensation of l-serine (1a), l-threonine (1b) and l-cysteine (1c) methyl esters with formaldehyde afforded N-acyl-pseudoprolines 7-19 in various yields. These 2:3 adducts can be considered as synthetic equivalents of oxaproline and thiaproline moieties. The present work revealed the versatile behaviour of the two 2:3 adducts as a consequence of the ring-chain tautomerism occurring in the five- and/or seven-membered rings.

Papuamides A-D, HIV-inhibitory and cytotoxic depsipeptides from the sponges Theonella mirabilis and Theonella swinhoei collected in Papua New Guinea

The novel cyclic depsipeptides papuamides A (1), B (2), C (3), and D (4) have been isolated from Papua New Guinea collections of the sponges Theonella mirabilis and Theonella swinhoei. Their structures were determined by a combination of spectroscopic analysis and chemical degradation and derivatization studies. In addition to glycine, alanine, and threonine, these peptides contain a number of unusual amino acids including 3,4- dimethylglutamine, β-methoxytyrosine, 3-methoxyalanine, and 2,3- diaminobutanoic acid or 2-amino-2-butenoic acid residues. Papuamides A-D (1- 4) are also the first marine-derived peptides reported to contain 3- hydroxyleucine and homoproline residues. These peptides also contain a previously undescribed 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid moiety N-linked to a terminal glycine residue. Papuamides A (1) and B (2) inhibited the infection of human T-lymphoblastoid cells by HIV-1(RF) in vitro with an EC50 of approximately 4 ng/mL. Compound 1 was also cytotoxic against a panel of human cancer cell lines with a mean IC50 of 75 ng/mL.

Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure, 3-Substituted (2S,3R)-N-Methylserine Esters

A novel method for the synthesis of N-methylserines has been developed.The oxazolidines 4 are formed by condensation of the serine methyl esters 1 with formaldehyde.These intermediates are subsequently reduced to the N-methylserine methyl esters 9 by an acid-catalyzed ring opening via their iminium ions 2 with triethylsilane/trifluoroacetic acid. key words: Serine derivatives; bislactim ether method.