Abstract: The present invention generally relates to compounds that include one or more thermally labile protecting groups, compositions including the compounds, methods of making the compounds and compositions and methods of using the compounds and compositions. In one aspect, the present invention is directed to a compound of the structure XO—CH2—SM-B-A. The substituent X is H, an acid labile protecting group, a solid support, —P(O—R1)NR2R3, —P(O)(OH)H, —P(O)(OR1)H, —P(O)(OH)2, —P(O)(OH)O—P(O)(OH)OP(O)(OH)2 or salts thereof. The substituent R1 is CNE (i.e., cyanoethyl), alkyl, or heteroalkyl and R2 and R3 are independently alkyl. The substituent SM is a sugar moiety or analogue thereof that is not a natural furanosyl, B is a base moiety or analogue thereof, and A is a moiety attached to a nitrogen on or in the base moiety of the structure —C(O)OR4, wherein R4 is tertiary alkyl.

Abstract: Pharmaceutical compositions and methods of using them. Lipid formulations of a glutathione analog and methods of manufacturing them. Their use to stimulate hematopoiesis, protect hematopoietic cells from damage caused by radiation or chemotherapy, or potentiate the stimulatory action of one or a combination of cytokines on colony formation by hematopoietic progenitor cells, protect a subject from a destructive effect of a chemotherapeutic agent or irradiation, or to potentiate the effect of a chemotherapeutic agent.

Abstract: Pharmaceutical compositions and methods of using them. Lipid formulations of a glutathione analog and methods of manufacturing them. Their use to stimulate hematopoiesis, protect hematopoietic cells from damage caused by radiation or chemotherapy, or potentiate the stimulatory action of one or a combination of cytokines on colony formation by hematopoietic progenitor cells, protect a subject from a destructive effect of a chemotherapeutic agent or irradiation, or to potentiate the effect of a chemotherapeutic agent.

Abstract: Compounds of the formula ##STR1## or the alkyl (1-6C), alkenyl (1-6C), or arylalkyl (7-12C) amides or salts including the cycloamido forms thereof;whereinn is 1 or 2;whereinwhen n is 1, X is a mono- or disubstituted or unsubstituted hydrocarbyl (1-20C) moiety optionally containing 1 or 2 nonadjacent heteroatoms (O, S or N), and wherein said substitution is selected from the group consisting of halo, OR, and SR, wherein R is H or lower alkyl (1-4C); when n is 2, one X is as above defined and the other X is lower alkyl (1-4C);Y is selected from the group consisting of ##STR2## wherein m is 1 or 2; andAA.sub.C is an amino acid coupled through a peptide bond to the remainder of the compound of formula 1, are useful as affinity ligands, elution reagents, solution inhibitors, diagnostic reagents and therapeutics. These compounds and analogous tripeptide glutathione analogs can be used as members of panels to obtain specific characteristic profiles for various glutathione-S-transferases.

Abstract: Compounds of the formula ##STR1## and the esters, amides, amide/esters and salts thereof, wherein YCO is .gamma.-glu or .beta.-asp;G* is phenylglycine or glycine;Z is CH.sub.2, O or S; andX is a hydrocarbon radical selected from C.sub.6 -C.sub.8 alkyl or selected aromatic groupsare useful in modulating hematopoiesis in bone marrow, mitigating the bone-marrow-destructive effects of a chemotherapeutic agent, and in potentiating the toxicity of chemotherapeutic agents.

Abstract: Compounds of the formula ##STR1## or of the formula ##STR2## or the amides, esters or salts thereof, wherein: S.sup.x is S.dbd.O, O.dbd.S.dbd.O, S.dbd.NH, HN.dbd.S.dbd.O, Se.dbd.O, O.dbd.Se.dbd.O, Se.dbd.NH, HN.dbd.Se.dbd.O, S.sup.+ R.sup.3 wherein R.sup.3 is alkyl (1-6C) or O--C.dbd.O or HN--C.dbd.O;each R of R.sup.1, and R.sup.2 is independently H or a noninterfering substituent;wherein (conj) represents a conjugated system capable of transmitting electrons;n is 0 or 1;YCO is selected from the group consisting of .gamma.-Glu, .gamma.-Glu-Gly, Glu, Glu-Gly, .beta.Asp, .beta.-Asp-Gly, Asp and Asp-Gly;AA.sub.C is an amino acid linked through a peptide bond to the remainder of said compound of Formula 1; andN(Z) represents a reduced nitrogen-containing leaving group and L represents an electron-withdrawing leaving group,are useful as prodrugs and to generate active components released by the activity of glutathione S-transferase.

Abstract: Compounds wherein a biologically active molecule is coupled to a glutathione analog through a conjugated system which permits activation of the biologically active molecule while retaining the biologically active molecule tethered to the glutathione analog are useful as tethered prodrugs that slow the rate of clearance of an active biomolecule through the multidrug resistance pump.

Abstract: Solid phase supported synthesis of peptides and other molecules using protecting groups comprising p-nitrobenzyl is described.

Abstract: A method to potentiate the effect of a chemotherapeutic agent in a tumor cell, which method comprises administering to said tumor cell, along with said chemotherapeutic agent, a potentiating amount of a compound of the formula: ##STR1## or an amide, ester or hybrid amide/ester thereof, wherein X is a hydrocarbon radical optionally substituted on any aromatic moiety contained therein; Y--CO is .gamma.-Glu or .beta.-Asp and AA.sub.C is an amino acid, preferably glycine, phenylglycine, .beta.-alanine, alanine or phenylalanine is disclosed.Similar compounds can also be used to selectively exert cytotoxicity versus target cells as compared to nontarget cells and also to elevate the production of GM progenitors in bone marrow of mammalian subjects.

Abstract: Compounds of the formula ##STR1## and the esters, amides, amide/esters and salts thereof, wherein YCO is .gamma.-glu or .beta.-asp;G* is phenyl glycine or glycine;Z is CH.sub.2, O or S; andX is a hydrocarbon radical of 1-20 C;are useful in stimulating the differentiation of bone marrow, mitigating the bone-marrow-destructive effects of a chemotherapeutic agent, and in potentiating the toxicity of chemotherapeutic agents.

Abstract: Compounds of the formula ##STR1## or the alkyl (1-6C), alkenyl (1-6C), or arylalkyl (7-12C) amides or salts including the cycloamido forms thereof;wherein n is 1 or 2;wherein when n is 1, X is a mono- or disubstituted or unsubstituted hydrocarbyl (1-20C) moiety optionally containing 1 or 2 nonadjacent heteroatoms (O, S or N), and wherein said substitution is selected from the group consisting of halo, OR, and SR, wherein R is H or lower alkyl (1-4C); when n is 2, one X is as above defined and the other X is lower alkyl (1-4C);Y is selected from the group consisting of ##STR2## wherein m is 1 or 2; and AA.sub.C is an amino acid coupled through a peptide bond to the remainder of the compound of formula 1, are useful as affinity ligands, elution reagents, solution inhibitors, diagnostic reagents and therapeutics. These compounds and analogous tripeptide glutathione analogs can be used as members of panels to obtain specific characteristic profiles for various glutathione-S-transferases.

Abstract: A process for preparing a trinucleotide phosphoramidite comprising reacting a 3',5'-dihydroxy dinucleoside with a nucleoside 5'-phosphoramidite; oxidizing this trinucleotide phosphite to produce the 3'-hydroxyl trinucleotide; and finally converting the 3'-hydroxy trinucleotide to the 3'-phosphoramidite derivative. Such trinucleotide phosphoramidites provide a convenient route for synthesizing oligonucleotides with randomized codons at specified positions.

Abstract: The invention is a method which allows the attachment of an alcohol to a substrate by the use of which chemical and/or enzymatic transformations of the alcohol are facilitated, and subsequently the modified alcohol can be released, if desired, under exquistely mild conditions, after selective removal of a protecting group from an expulsion promoting amino group.

Abstract: Compounds of the formula: ##STR1## or a salt thereof, wherein n is 1 or 2;wherein when n is 1, X is a mono- or disubstituted or unsubstituted C.sub.1-20 hydrocarbon radical wherein any substitution is selected from the group consisting of halo, OR, and SR, wherein R is H or C.sub.1-4 alkyl;and wherein, when n is 2, one X is defined as for n=1 and the other X is lower C.sub.1-4 alkyl; ##STR2## wherein m is 1 or 2; AA.sub.C is an amino acid coupled through a peptide bond to the remainder of the compound of Formula (1) selected from the group consisting of glycine, valine, alanine, 4-aminobutyric acid, aspartic acid, phenylglycine, histidine, tryptophan, tyrosine, and phenylalanine, wherein the phenyl group of phenylalanine or phenylglycine may optionally contain a single substitution selected from the group consisting of halo, OR, and SR, wherein R is H or C.sub.1-4 alkyl;with the proviso that if Y is ##STR3## AA.sub.C is not Gly; and if Y is ##STR4## and X is benzyl, AA.sub.

Abstract: Compounds of the formula ##STR1## or the alkyl (1-6 C), alkenyl (1-6 C), or arylalkyl (7-12 C) amides or salts including the cycloamido forms thereof;wherein n is 1 or 2;wherein when n is 1, X is a mono- or disubstituted or unsubstituted hydrocarbyl (1-20 C) moiety optionally containing 1 or 2 nonadjacent heteroatoms (O, S or N), and wherein said substitution is selected from the group consisting of halo, OR, and SR, wherein R is H or lower alkyl (1-4 C); when n is 2, one X is as above defined and the other X is lower alkyl (1-4 C);Y is selected from the group consisting of ##STR2## wherein m is 1 or 2; and AA.sub.C is an amino acid coupled through a peptide bond to the remainder of the compound of formula 1, are useful as affinity ligands, elution reagents, solution inhibitors, diagnostic reagents and therapeutics. These compounds and analogous tripeptide glutathione analogs can be used as members of panels to obtain specific characteristic profiles for various glutathione-S-transferases.

Abstract: Compounds of the formula: ##STR1## or the amides, esters or salts thereof, wherein: L is an electron withdrawing leaving group;S.sup.x is S.dbd.O, O.dbd.S.dbd.O, S.dbd.NH, HN.dbd.S.dbd.O, Se.dbd.O, O.dbd.Se.dbd.O, Se.dbd.NH, HN.dbd.Se.dbd.O, S.sup.+ R.sup.4 wherein R.sup.4 is alkyl (1-6C), or O--C.dbd.O or HN--C.dbd.O;each R of R.sup.1, R.sup.2 and R.sup.3 is independently H or a noninterfering substituent;n is 0, 1 or 2;Y is selected from the group consisting of ##STR2## wherein m is 1 or 2; and AA.sub.C is an amino acid linked through a peptide bond to the remainder of said compound of formula 1, are disclosed.These compounds are useful prodrugs for selective treatment of target tissues which contain compatible glutathione S-transferase (GST) isoenzymes, and simultaneously elevate the levels of GM progenitor cells in bone marrow.

Abstract: Compounds of the formula: ##STR1## or the amides, esters or salts thereof, wherein: L is an electron withdrawing leaving group;S.sup.x is S=O, O=S=O, S=NH, HN=S=O, Se=O, O=Se=O, Se=NH, HN=Se=O, S+R.sup.4 wherein R.sup.4 is alkyl (1-6 C), or O--C=O or HN--C=O;each R of R.sup.1, R.sup.2 and R.sup.3 is independently H or a noninterfering substituent;n is 0, 1 or 2;Y is selected from the group consisting of ##STR2## wherein m is 1 or 2; and AA.sub.C is an amino acid linked through a peptide bond to the remainder of said compound of formula 1, are dislosed.These compounds are useful prodrugs for selective treatment of target tissues which contain compatible glutathione S-transferase (GST) isoenzymes.