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Endoplasmic reticulum-associated degradation of glycoproteinsbearing Man5GlcNAc2 and Man9GlcNAc2 species in the MI8-5 CHO cell line Franc¸ois Foulquier, Sandrine Duvet, Andre´ Klein, Ann

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Endoplasmic reticulum-associated degradation of glycoproteins

bearing Man5GlcNAc2 and Man9GlcNAc2 species in the MI8-5

CHO cell line

Franc¸ois Foulquier, Sandrine Duvet, Andre´ Klein, Anne-Marie Mir, Fre´de´ric Chirat and Rene´ Cacan Unite´ de Glycobiologie Structurale et Fonctionnelle, CNRS-UMR 8576, IFR 118, GDR CNRS 2590, Universite´ des Sciences

et Technologies de Lille, Villeneuve d’Ascq, France

Endoplasmic reticulum-associated degradation of newly

synthesized glycoproteins has been demonstrated previously

using various mammalian cell lines Depending on the cell

type, glycoproteins bearing Man9 glycans and glycoproteins

bearing Man5 glycans can be efficiently degraded Awide

variety of variables can lead to defective synthesis of

lipid-linked oligosaccharides and, therefore, in mammalian cells,

species derived from Man9GlcNAc2 or Man5GlcNAc2 are

often recovered on newly synthesized glycoproteins The

degradation of glycoproteins bearing these two species has

not been studied We used a Chinese hamster ovary cell

line lacking Glc-P-Dol-dependent glucosyltransferase I to

generate various proportions of Man5GlcNAc2 and Man9GlcNAc2 on newly synthesized glycoproteins By studying the structure of the soluble oligomannosides pro-duced by degradation of these glycoproteins, we demon-strated the presence of a higher proportion of soluble oligomannosides originating from truncated glycans, showing that glycoproteins bearing Man5GlcNAc2 glycans are degraded preferentially

Keywords: degradation signal; lipid intermediates; manno-sidase activity; N-glycosylation; soluble oligomannosides

The N-glycosylation process is characterized by the

transfer en bloc of a preassembled oligosaccharide on

to a nascent protein According to the specificity of the

oligosaccharyltransferase, it has been demonstrated

in vitro that a wide variety of assembly intermediates

Glc(0–3)Man(0–9)GlcNAc2-PP-Dol can serve as the

donor substrate for N-linked glycosylation [1] In vivo,

Gilmore and coworkers have determined that

oligosacch-aryltransferase shows a preference for the full length

oligosaccharide substrate [2]

Once transferred to proteins, the N-linked

oligosaccha-rides play the role of information carrier in the quality

control mechanism of N-glycoproteins in the endoplasmic

reticulum (ER) Indeed, monoglucosylated oligosaccharides

generated either after sequential action of

glucosi-dase I and II or by the soluble UDP-Glc–glycoprotein

glucosyltransferase (UGGT) can be ligands for the mole-cular lectin-like chaperones calnexin and calreticulin until proper folding of the N-glycoproteins [3,4]

With N-glycoproteins that fail to fold correctly, a Man8GlcNAc2 species is generated by an ER a1,2-manno-sidase, probably ER mannosidase I, and this constitutes a putative degradation signal [5] Recently, Frenkel et al [6] demonstrated that the degradation of unstable N-glycopro-teins accumulated in a rough ER subcompartment (QC compartment) involves trimming of the sugar chain to Man(6–5)GlcNAc2 species Furthermore, by using a mutant cell line that synthesizes truncated Man5GlcNAc2, Ermon-val et al [7] showed that the degradation of a soluble form

of ribophorin I required the formation of Man4GlcNAc2 After the trimming of Man residues, these misfolded N-glycoproteins are then degraded by a specific pathway named endoplasmic reticulum-associated degradation (ERAD) This pathway involves a deglycosylation step located in the cytosol, and the soluble oligomannosides released by this process were then submitted to the action of a 1,4-dideoxy-1,4-imino-D-mannitol (DIM)-sensitive cytosolic mannosidase [8], leading to the formation of a specific Man5GlcNAc1 isomer [9] before entering the lysosomal compartment [10]

Thus, it appears that at least three oligomannoside structures may be involved as degradation signal for ERAD (Man8GlcNAc2 and Man6GlcNAc2 for glycoproteins bearing Man9 species and Man4GlcNAc2 for glycoproteins bearing Man5 species) However, this has been observed using different cell lines So we decided to study the degradation of N-glycoproteins when these oligomannoside structures are both transferred to newly synthesized glyco-proteins in the same cell line

Correspondence to R Cacan, Unite´ de Glycobiologie Structurale et

Fonctionnelle, CNRS-UMR 8576, Universite´ des Sciences et

Tech-nologies de Lille, F-59655 Villeneuve d’Ascq Cedex, France.

Fax: + 33 3 20 43 65 55, Tel.: + 33 3 20 43 44 30,

E-mail: rene.cacan@univ-lille1.fr

Abbreviations: CHO, Chinese hamster ovary; DIM,

1,4-dideoxy-1,4-imino- D -mannitol; Dol, dolichol; ERAD, endoplasmic

reticulum-associated degradation; ER, endoplasmic reticulum; LLO, lipid-linked

oligosaccharide; PNGase, peptide N-glycanase F; UGGT,

UDP-glucose–glycoprotein glucosyltransferase; UPR,

unfolded protein response.

Enzymes: peptide N-glycanase F (PNGase; EC 3.2.2.18);

b-galactosi-dase (EC 3.2.1.23); b-hexosaminib-galactosi-dase (EC 3.2.1.30).

(Received 15 September 2003, revised 21 October 2003,

accepted 21 November 2003)

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Experimental procedures

Materials

[2-3H]Man (429 GBqÆmmol)1) was from Amersham (Little

Chalfont, Bucks, UK) Trypsin and castanospermine were

from Sigma Kifunensine and DIM were from ICN, Orsay,

France Peptide N-glycanase F (PNGase) was from Biolabs

b-Galactosidase and b-hexosaminidase (both isolated from

Jack bean) were from Oxford GlycoSystems (Abingdon,

Oxon, UK) Glucosidase II purified from rat liver was a gift

from T Butters (Oxford Glycobiology Institute, University

of Oxford, UK)

Cell culture

The Glc-P-Dol-dependent glucosyltransferase I-deficient

mutant Chinese hamster ovary (CHO) cell line (MI8-5)

was a gift from S S Krag (Johns Hopkins University,

Baltimore, MD, USA) This cell line was grown in

a-minimal essential medium (Gibco-BRL) supplemented

with 10% (v/v) fetal bovine serum, at 34C under 5%

CO2

Metabolic labeling of oligosaccharides and pulse-chase

experiments

For this purpose, MI8-5 cells were routinely grown in

10-cm Petri dishes Cells were preincubated at low Glc

concentration (0.175 mM) for different times and then

metabolically labeled for 1 h with 3.6 GBqÆmL)1 (4 lM)

[2-3H]Man at the same Glc concentration For pulse-chase

experiments, the radioactive culture medium was replaced

by a-minimal essential medium containing the

physiolo-gical Glc concentration (5 mM) supplemented with 5 mM

Man When used, kifunensine (20 lM) and DIM (1 mM)

were present throughout the experiment (preincubation,

pulse and chase) Sequential extraction and purification of

oligosaccharide material were achieved as previously

described [9]

Analysis of oligosaccharide material and glycosidase

treatments

Soluble oligomannoside fractions obtained after the

sequential extraction were desalted on Bio-Gel P2 eluted

with 5% (v/v) acetic acid Glycoprotein fractions obtained

at the end of the sequential extraction were digested with

trypsin (1 mgÆmL)1) in 0.1M ammonium bicarbonate

buffer, pH 7.9, overnight at room temperature

Elution of the radiolabeled oligosaccharides was moni-tored by continuous-flow detection of the radioactivity with a flo-one b-detector (Packard, Les Ullis, France) For the sequential glycosidase treatments, oligosaccha-rides released after PNGase digestion were first dissolved

in 2Macetic acid, and hydrolysis was carried out at 80C for 2 h to release sialyl residues Incubation with 0.1 U b-galactosidase was performed in 20 lL 100 mM sodium acetate buffer, pH 3.5, overnight at 37C Then 0.1 U b-hexosaminidase was added for an additional overnight incubation The incubation mixture was then analyzed by HPLC

Results

Synthesis and transfer of Man5GlcNAc2 species

in the MI8-5 cell line

We have demonstrated previously that MI8-5 CHO cells are deficient in Glc-P-Dol-dependent glucosyltransferase I and that the glycans transferred on to glycoproteins are thus non-glucosylated [12] By using incubation with labeled Man at low Glc concentration (0.175 mM), we now observed that Man5GlcNAc2-PP-Dol, an inter-mediate in the formation of Man9GlcNAc2-PP-Dol, was transferred to glycoprotein acceptors (Fig 1A,E) Recently, Shang et al [13] reported that, when cells were preincubated at low Glc concentration, the truncated LLOs were extended as a consequence of activation of the unfolded protein response (UPR) To obtain various proportions of Man5 and Man9 species on newly synthesized glycoproteins, MI8-5 cells were preincubated for up to 120 min at low Glc concentration (0.175 mM) and incubated with labeled Man for 60 min Figure 1 shows that, when the preincubation period was increased, the UPR was activated, because, after 20, 40 and 120 min

of Glc deprivation, the radioactivity shifted from the truncated species (Man3GlcNAc2-PP-Dol and Man5Glc-NAc2-PP-Dol) to Man9GlcNAc2-PP-Dol (Fig 1A–C)

To demonstrate that glycans bound to proteins are not the result of modification by processing enzymes, the same experiment was performed in the presence of kifunensine, an inhibitor of the demannosylation process Figure 1D,H shows that incubation in the presence of

20 lMkifunensine did not affect the proportion of Man5 and Man9 species bound to LLOs and glycoproteins This demonstrates that both species were transferred with different proportions according to the relative abundance

of each species present on the LLOs (Fig 1E–G)

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Dual fate of Man5GlcNAc2 bound to glycoproteins

in the MI8-5 cell line

As described previously for MI8-5 cells, the transfer of

Man9GlcNAc2 to glycoproteins led to the formation of

Man8GlcNAc2 and Glc1Man9GlcNAc2, as the formation

of monoglucosylated glycans by UGGT was not affected

in this cell line In the same manner, the transfer of

Man5GlcNAc2 species to glycoproteins was confirmed by

the presence of three peaks: Man4GlcNAc2,

Man5Glc-NAc2 and peak X migrating as Glc1Man5GlcMan5Glc-NAc2

(Fig 1E–H)

To demonstrate that peak X may be the result of the

reglucosylation of the Man5GlcNAc2 species, MI8-5 cells

were metabolically labeled with [2-3H]Man with or without

100 lgÆmL)1castanospermine, an inhibitor of glucosidases I

and II In the presence of castanospermine, the levels of

both Glc1Man9GlcNAc2 and peak X were increased

(Fig 2A,B) Under these conditions, the decreasing

amounts of Man9GlcNAc2 and Man5GlcNAc2 correlated

with the increasing amounts of Glc1Man9GlcNAc2 and

peak X, respectively Furthermore, as expected, peak X and

Glc1Man9GlcNAc2 were completely sensitive to treatment with purified glucosidase II, which resulted in Man5Glc-NAc2 and Man9GlcMan5Glc-NAc2, respectively (Fig 2C) As Glc-P-Dol-dependent glucosyltransferase was not active

in MI8-5 cells, the monoglucosylated species detected on glycoproteins could only originate from the action of UGGT Furthermore, when the incubation was performed

in the presence of 20 lM kifunensine, the formation of Man4GlcNAc2 and Man8GlcNAc2 species was strongly inhibited (Fig 1H) This suggests the involvement of class I mannosidase in these demannosylation processes [14]

Fate of glycoproteins bearing Man5GlcNAc2 and Man9GlcNAc2

Depending on the preincubation time at low Glc concen-tration, various proportions of Man5GlcNAc2 and Man9GlcNAc2 species could be transferred to proteins

To obtain an equal distribution of the radioactivity between the Man5 and Man9 populations bound to the glycopro-teins, cells were preincubated for 40 min in 0.175 mMGlc, labeled for 1 h, and chased in the culture medium (5 m

Fig 1 HPLC analysis of LLO and oligo-mannoside species bound to newly synthesized glycoproteins during Glc deprivation of MI8-5 cells MI8-5 cells were preincubated in 0.175 m M Glc for 20, 40 and 120 min, and then pulsed for 1 h with [2- 3 H]Man in the same medium Cells were then submitted to the sequential extraction procedure Oligo-mannosides bound to LLO (A, B, C and D) and glycoproteins (E, F, G and H) were ana-lyzed by HPLC as described in Experimental procedures (D) and (H) correspond to the pattern of oligomannosides bound to LLO and glycoproteins, respectively, when the incubation was performed in the presence of

20 l M kifunensine after a 20 min preincuba-tion G1M9 indicates oligomannosides con-taining one Glc, nine Man, and two GlcNAc residues M3, M4, M5, M8 and M9 indicate oligomannosides containing three, four, five, eight and nine Man residues and two GlcNAc residues, respectively X indicates an uniden-tified peak.

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Glc with 5 mMMan) for 0, 3 and 6 h At each time point,

glycans bound to glycoproteins were released by PNGase

and sequentially treated to release sialic acid, galactose and

GlcNAc residues As previously described [15], the

appear-ance of Man3GlcNAc2 species after these treatments

reveals the level of Golgi processing Figure 3 shows that

the percentage of radioactivity bound to Man3GlcNAc2

species increased from 18% after the pulse to 38% after the

6 h chase Formation of complex-type glycans correlated

with the decrease in the percentage of radioactivity

associ-ated with oligomannoside-type glycans, mainly the Man9

population If we look at the end products of processing,

most of the Man5GlcNAc2 was converted into

Man4Glc-NAc2, in contrast with the small amount of Man6GlcNAc2

originating from the Man9GlcNAc2 species

ERAD of glycoproteins bearing Man5 and Man9

populations in MI8-5 cells

The N-glycosylation process is accompanied by the release

of soluble oligomannosides At least some of this soluble

material has been shown to originate from glycoprotein

degradation [16,17] after the quality control mechanism

Figure 4Ashows the pattern of oligomannosides bound to

glycoproteins after 20 min of preincubation at 0.175 mM

Glc followed by 1 h of labeling and a 1 h chase in culture

medium containing 5 mMGlc and 5 mMMan Under these

conditions as described previously [17], the profile of soluble

oligomannosides contained three major species:

Man4Glc-NAc1, Man5GlcNAc1 and Glc1Man5GlcNAc1 (Fig 4B)

The smaller species (from Man3GlcNAc1 to

Man1Glc-NAc1) correspond to lysosomal degradation of the soluble

oligomannosides, as previously demonstrated [18] As these

species may result from the action of cytosolic mannosidase

[8], the same experiment was performed in the presence of

DIM to avoid cytosolic demannosylation of glycans

released during the degradation process Figure 4C shows

the profile of soluble oligomannosides when the same

experiment was performed in the presence of 1 mMDIM

Although the pattern of oligosaccharides bound to

glyco-proteins was not affected by the inhibitor (not shown),

Man5 and Man9 species were recovered in the soluble

oligomannoside fraction However, if we compare the

pattern of soluble oligomannosides with that obtained with

glycans bound to proteins (Fig 4C,A, respectively), it is

clear that a higher proportion of soluble oligomannosides

originate from the Man5 population than from the Man9

population

However, it has been shown that some of these soluble oligomannosides may originate from hydrolytic activity of the oligosaccharyltransferase complex using water as accep-tor for the oligosaccharide-PP-Dol donor [19] As glucosy-lated oligomannosides are present only on glycoproteins in MI8-5 cells, Glc1Man5GlcNAc1 and Glc1Man9GlcNAc1 can be used as markers for glycoprotein degradation Table 1 shows that the ratio Glc1Man5GlcNAc1/

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Glc1Man9GlcNAc1 obtained with soluble

oligomanno-sides was twofold higher than the ratio

Glc1Man5Glc-NAc2/Glc1Man9GlcNAc2 obtained with the glycoprotein

pattern This indicates that, when glycoproteins bearing

Man9 and Man5 are synthesized in the same cell line, those

bearing Man5 are more efficiently degraded

Furthermore, when various proportions of Man5 were

transferred to glycoproteins as a result of different

preincu-bation times at low Glc concentration, a direct relationship

was observed between the level of soluble oligomannosides

released and the proportion of Man5 species bound to the

glycoprotein fraction (Fig 4D)

Glycoproteins bearing only Man9 species can be obtained

in two ways: (a) induction of UPR by extensive

preincuba-tion at low Glc concentrapreincuba-tion (this treatment produces

extension of oligomannosides bound to lipid intermediates)

as in Fig 4D (0% of Man5 population); (b) incubation of

cells in the culture medium (5 mMGlc) which considerably

reduces the labeling In the two cases, glycoprotein

degra-dation, measured by the ratio radioactivity bound to soluble

oligomannosides/radioactivity bound to glycoproteins, is

the same (10–13%) As to the physiological relevance of the

incubation conditions used, this result suggests that Glc

deprivation does not significantly affect the degradation of

glycoproteins

Discussion

The synthesis of oligomannosides linked to lipid

inter-mediates depends on several cellular and extracellular

variables The Glc concentration in the extracellular

medium [20], the capacity of the cell to synthesize the

different metabolic precursors (GDP-Man, UDP-Glc,

Man-P-Dol, Glc-P-Dol), and the variations in the level of

expression of the various glycosytransferases, as observed

in patients with congenital disorders of glycosylation

[21,22], are variables that can modify the quality of the

LLO donors

However, several mechanisms avoid the transfer of truncated lipid donors, especially Man5GlcNAc2, to pro-teins: the activation of UPR, which promotes extension of such truncated LLO intermediates to Glc3Man9GlcNAc2-PP-Dol [13]; the high turnover rate of lipid donors These adaptive events involve only the lipid intermediate donors and not the glycans bound to the protein moiety Thus the fate of glycoproteins bearing Man5GlcNAc2glycans has to

be envisaged

For this, we decided to generate glycoproteins bearing Man5 and Man9 populations in the same cell type To avoid preferential transfer of glucosylated species from LLO, we used MI8-5 CHO cells deficient in Glc-P-Dol-dependent glucosyltransferase I As observed previously for other cell lines [23], the stress induced by preincubation at low Glc concentration leads to a cellular response named UPR, the first level of which is the extension of LLOs Depending on the preincubation time, various proportions

of Man5GlcNAc2 and Man9GlcNAc2 are transferred to proteins The ER processing of these two species has been studied As expected, Man9 species gave Glc1Man9Glc-NAc2, which revealed the action of UGGT For Man5Glc-NAc2 species, although it has been claimed that UGGT is not active on this species, we have clearly demonstrated the formation of Glc1Man5GlcNAc2 The formation of this species has been observed previously in mutant cell lines [24,25] However, this result indicates that this reglucosy-lation step is not specific to the Man-P-Dol-deficient mutant cell line, but can be observed when Man9 species are present on newly synthesized glycoproteins Similarly, the Man9 and Man5 species undergo demannosylation reactions Man5GlcNAc2 is converted into Man4Glc-NAc2, which cannot be reglucosylated, and Man9Glc-NAc2 can be demannosylated first into Man8GlcMan9Glc-NAc2 and, after a longer chase period, into Man6GlcNAc2 This species has been observed on resident glycoproteins, as demonstrated for ribophorin I [26] and unstable glyco-proteins [6]

Fig 3 Evolution of Man9 and Man5 populations bound to proteins during a pulse-chase experiment MI8-5 CHO cells were pulse-labeled with [2- 3 H]Man for 1 h after 40 min of preincubation in 0.175 m M Glc (T0 h) and chased in the culture medium containing 5 m M Glc and 5 m M Man for 3 and 6 h (T3 h and T6 h, respectively) The cells were then submitted to the sequential extraction procedure Glycans were released from the glycoprotein fraction by the action of PNGase They were then analyzed by HPLC after mild acid treatment and the sequential action of b-galactosidase and b-hexosaminidase as described in Experimental procedures M3, M4, M5, M6, M7, M8, M9 indicate oligomannosides with three, four, five, six, seven, eight and nine Man residues and two GlcNAc residues at the reducing end G1M5 indicates oligomannosides with five Man and two GlcNAc residues at the reducing end and one Glc residue, respectively G1M9 indicates oligomannosides with one Glc residue and nine Man and two GlcNAc residues at the reducing end.

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Most of the evidence for the occurrence of degradation

signals involved in ERAD has been obtained by studying

the effect of inhibitors of demannosylation (kifunensine and

deoxymannojirimycine) on glycoprotein degradation As we

demonstrated that the glucosylated soluble

oligomanno-sides released during the N-glycosylation process of MI8-5

originate only from glycoprotein degradation [17], we

compared the ratio Glc1Man5/Glc1Man9 on glycoproteins

and the soluble oligomannoside fractions in experiments

performed in the presence of DIM, an inhibitor of the

cytosolic mannosidase We observed that glycoproteins

bearing Man5 were more efficiently degraded (twofold)

than those bearing Man9 It is noteworthy that the release

of the glucosylated species was accompanied by the release

of Man8–5GlcNAc1 and Man4GlcNAc1, which are puta-tive degradation signals for glycoproteins bearing Man9 and Man5, respectively As we only took into account mono-glucosylated species, the degradation of the Man5 popula-tion was probably underestimated

We have reported previously [27] that the level of soluble oligomannosides released during N-glycosylation is higher

in Man-P-Dol-deficient cell lines than in wild-type cells, which are able to elongate their lipid intermediates We have also demonstrated that the pattern of these oligomannosides

is related to the pattern of the glycans bound to the newly

Table 1 Radioactivity bound to Glc1Man5 and Glc1Man9 species during chase experiments in MI8-5 cells in the presence of 1 m M DIM MI8-5 cells in the presence of 1 m M DIM were pulsed for 1 h and chased in culture medium containing 5 m M Glc and 5 m M Man for 1 h after 20 min preincubation with 0.175 m M Glc Cells were then sub-mitted to the sequential extraction procedure The radioactivity bound

to Glc1Man5 and Glc1Man9 species was measured after counting of the glycoprotein and soluble oligomannoside fractions, taking into account the percentage of these species as determined by HPLC Values (d.p.m.) from three different experiments are shown.

Glc1Man5 Glc1Man9

Glc1Man5/ Glc1Man9 Glycoprotein fraction 113512 127650 0.88

114070 134000 0.85

114418 134350 0.85 Soluble oligomannoside

released during the chase experiment

14520 7100 2.04

13250 8206 1.61

13510 8214 1.64

0.175 m M Glc before the 1-h pulse (from 120 min preincubation for 0% Man5 species to 20 min preincubation for 50% Man5 species).

OS, Soluble oligomannosides M4, M5, M6, M7, M8, M9 indicate oligomannosides with four, five, six, seven, eight and nine Man resi-dues and two GlcNAc resiresi-dues at the reducing end G1M5 indicates oligomannosides with five Man and two GlcNAc residues at the reducing end and one Glc residue, respectively G1M9 indicates oligo-mannosides with one Glc residue and nine Man and two GlcNAc residues at the reducing end M4Gn1, M5Gn1, M6Gn1, M7Gn1, M8Gn1, and M9Gn1 indicate oligomannosides with four, five, six, seven, eight and nine Man residues and one GlcNAc residue at the reducing end G1M5Gn1 and G1M9Gn1 indicate oligomannosides with one Glc residue, five or nine Man residues and one GlcNAc residue at the reducing end.

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synthesized glycoproteins [18] We have shown here that,

when Man5GlcNAc2 oligosaccharides are transferred to

glycoproteins in cells able to synthesize and transfer

Man9GlcNAc2, the glycoproteins bearing these truncated

glycans are preferentially degraded It means that the

mechanism of degradation found in mutant cells is also used

by normal cells

Acknowledgements

This work was supported by the Centre National de la Recherche

Scientifique and the Ministe`re de l’Education Nationale et de la

Recherche Technologique We are grateful to Dr J.-C Michalski

director of UMR 8576, Glycobiologie Structurale et Fonctionnelle.

We gratefully acknowledge Dr T Butters for generously supplying

glucosidase II, and Dr S S Krag for her gift of MI8-5 cell lines.

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